dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-31c4a896e83a45cebbddcb3318f26ca3 | CCOC(=O)Cn1ccc(=O)cc1.NN>>NNC(=O)Cn1ccc(=O)cc1 | C(C)OC(CN1C=CC(C=C1)=O)=O.O.NN>>O=C1C=CN(C=C1)CC(=O)NN | CCO[C:3](=[O:4])[CH2:5][n:6]1[cH:7][cH:8][c:9](=[O:10])[cH:11][cH:12]1.[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][n:6]1[cH:7][cH:8][c:9](=[O:10])[cH:11][cH:12]1 | CCOC(=O)Cn1ccc(=O)cc1.NN | NNC(=O)Cn1ccc(=O)cc1 | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | O=c1cc[nH]cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 98 | [{"value": 98.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (4-oxo-4H-pyridin-1-yl)-acetic acid ethyl ester (Bambury, Ronald E.; Edwards, Michael Louis; Miller, Laird Foulis. 4-Oxo-1-pyridinylpeniclliin and -cephalosporin derivatives. Ger. Offen. (1975)) in ethanol was reacted with hydrazine hydrate (1.2 equivalents) at rt for 72 h. The mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccncc1 | HO- | C(C)O | null | null | CCOC(=O)Cn1ccc(=O)cc1.NN>C(C)O>NNC(=O)Cn1ccc(=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-609e140f7df14979a2f7e483e38df976 | Cc1ncn(-c2ccc(Br)cc2C#N)c1C[N+](C)(C)C.NNC(=O)Cn1ccc(=O)cc1>>CC(C)OC(C)C.CO | BrC1=CC(=C(C=C1)N1C=NC(=C1C[N+](C)(C)C)C)C#N.[I-].O=C1C=CN(C=C1)CC(=O)NN>>CO.C(C)(C)OC(C)C | C[N+](C[c:3]1n(-c2ccc(Br)cc2C#N)cn[c:2]1[CH3:1])([CH3:6])[CH3:7].NN[C:8](Cn1cc[c:5](=[O:4])cc1)=[O:9]>>[CH3:1][CH:2]([CH3:3])[O:4][CH:5]([CH3:6])[CH3:7].[CH3:8][OH:9] | Cc1ncn(-c2ccc(Br)cc2C#N)c1C[N+](C)(C)C.NNC(=O)Cn1ccc(=O)cc1 | CC(C)OC(C)C.CO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5f0b96cddc733e76e41f5cbe2934f2b24f6ef872ca06299474a8de03841efc70 | 67d3fc410ee0472bd8349ad7cd324cf228a4809901339c7d9fd10e6877802389 | null | Br-c1:c:c:c(-n2:c:n:[c;H0;D3;+0:1](-[C;D1;H3:2]):[c;H0;D3;+0:3]:2-C-[N+](-C)(-[CH3;D1;+0:4])-[CH3;D1;+0:5]):c(-C#N):c:1.N-N-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-C-n1:c:c:[c;H0;D3;+0:8](=[O;H0;D1;+0:9]):c:c:1>>[C;D1;H3:2]-[CH;D3;+0:1](-[CH3;D1;+0:3])-[O;H0;D2;+0:9]-[CH;D3;+0:8](-[CH3;D1;+0:4])-[CH3;D1;+0:5].[CH3;D1;+0:6]-[OH... | 33 | [{"value": 33.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84d, [3-(4-bromo-2-cyano-phenyl)-5-methyl-3H-imidazol-4-ylmethyl]-trimethyl-ammonium; iodide (example 84c) was reacted with (4-oxo-4H-pyridin-1-yl)-acetic acid hydrazide. After evaporation of the solvent the residue was concentrated and chromatographed (SiO2, dichloromethane:methanol=100:0 to 9... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aromatic halide.Nitrile | Ether.Methanol | c1c[nH]cn1.c1ccccc1.c1ccncc1 | null | null | HBr | null | null | null | Cc1ncn(-c2ccc(Br)cc2C#N)c1C[N+](C)(C)C.NNC(=O)Cn1ccc(=O)cc1>>CC(C)OC(C)C.CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d37ce23a0404f77a3e8c04498ec18a9 | CCOC(=O)CN(C)C=O.NN>>CN(C=O)CC(=O)NN | C(C)OC(CN(C)C=O)=O.O.NN>>N(N)C(=O)CN(C=O)C | CCO[C:6]([CH2:5][N:2]([CH3:1])[CH:3]=[O:4])=[O:7].[NH2:8][NH2:9]>>[CH3:1][N:2]([CH:3]=[O:4])[CH2:5][C:6](=[O:7])[NH:8][NH2:9] | CCOC(=O)CN(C)C=O.NN | CN(C=O)CC(=O)NN | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | null | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6].[N;D1;H2:7]-[NH2;D1;+0:8]>>[N;D1;H2:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6] | 84 | [{"value": 84.0, "product": "N(N)C(=O)CN(C=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (formyl-methyl-amino)-acetic acid ethyl ester (Hay, Michael P.; Wilson, William R.; Denny, William A. Tetrahedron (2000), 56(4), 645-657) in ethanol was reacted with hydrazine hydrate (1.2 equivalents) at rt for 96 h. The mixture was concentrated and chromatographed (SiO2, dichloromethane... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | null | HO- | C(C)O | null | null | CCOC(=O)CN(C)C=O.NN>C(C)O>CN(C=O)CC(=O)NN |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e6263eeedfa48e0bf3a0ae5bdc1fadb | CCOC(=O)Cn1c(C)cc(C)cc1=O.NN>>Cc1cc(C)n(CC(=O)NN)c(=O)c1 | C(C)OC(CN1C(C=C(C=C1C)C)=O)=O.O.NN>>CC1=CC(N(C(=C1)C)CC(=O)NN)=O | CCO[C:8]([CH2:7][n:6]1[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:14][c:12]1=[O:13])=[O:9].[NH2:10][NH2:11]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6]([CH2:7][C:8](=[O:9])[NH:10][NH2:11])[c:12](=[O:13])[cH:14]1 | CCOC(=O)Cn1c(C)cc(C)cc1=O.NN | Cc1cc(C)n(CC(=O)NN)c(=O)c1 | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | O=c1cccc[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | null | [] | null | null | null | null | As described for example 112a, (4,6-dimethyl-2-oxo-2H-pyridin-1-yl)-acetic acid ethyl ester (Shusherina, N. P.; Slavyanova, O. V.; Petrova, L. K.; Levina, R. Ya. Zhurnal Organicheskoi Khimii (1972), 8(2), 387-9) in ethanol was reacted with hydrazine hydrate (1.2 equivalents) at rt for 120 h. The mixture was concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccncc1 | HO- | C(C)O | null | null | CCOC(=O)Cn1c(C)cc(C)cc1=O.NN>C(C)O>Cc1cc(C)n(CC(=O)NN)c(=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3ed0c45c9a6c4e9cb8a5baa9d1aa71a3 | COC(=O)C(O)C(F)(F)F.NN>>NNC(=O)C(O)C(F)(F)F | COC(C(O)C(F)(F)F)=O.O.NN>>FC(C(C(=O)NN)O)(F)F | CO[C:3](=[O:4])[CH:5]([OH:6])[C:7]([F:8])([F:9])[F:10].[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH:5]([OH:6])[C:7]([F:8])([F:9])[F:10] | COC(=O)C(O)C(F)(F)F.NN | NNC(=O)C(O)C(F)(F)F | null | null | C(CCC)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[O;D1;H1:4])-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8].[N;D1;H2:9]-[NH2;D1;+0:10]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[C:3](-[O;D1;H1:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[N;D1;H2:9] | 81 | [{"value": 81.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, methyl-3,3,3-trifluoro-DL-lactate in butanol was reacted with hydrazine hydrate (1.2 equivalents) at rt for 16 h. The mixture was concentrated and the title compound was obtained as a light yellow oil (yield: 81%). MS: m/e=158.0 [M]+.
Conditions: See reaction.notes.procedure_details.
Work... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | null | HO- | C(CCC)O | null | null | COC(=O)C(O)C(F)(F)F.NN>C(CCC)O>NNC(=O)C(O)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-46c3720c154f4449815957fe8e3872cb | COC(=O)C(C)n1cncn1.NN>>CC(C(=O)NN)n1cncn1 | COC(C(C)N1N=CN=C1)=O.O.NN>>N1(N=CN=C1)C(C(=O)NN)C | CO[C:3]([CH:2]([CH3:1])[n:7]1[cH:8][n:9][cH:10][n:11]1)=[O:4].[NH2:5][NH2:6]>>[CH3:1][CH:2]([C:3](=[O:4])[NH:5][NH2:6])[n:7]1[cH:8][n:9][cH:10][n:11]1 | COC(=O)C(C)n1cncn1.NN | CC(C(=O)NN)n1cncn1 | null | null | C(CCC)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1nc[nH]n1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7;a:4])-[C;D1;H3:5].[N;D1;H2:6]-[NH2;D1;+0:7]>>[#7;a:4]-[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[N;D1;H2:6] | 91 | [{"value": 91.0, "product": "N1(N=CN=C1)C(C(=O)NN)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (rac.)-2-[1,2,4]triazol-1-yl-propionic acid methyl ester in butanol was reacted with hydrazine hydrate (1.2 equivalents) at rt for 16 h. The mixture was concentrated and triturated with toluene to afford the title compound as a white solid (yield: 91%). MS: m/e=155.0 [M]+.
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1nc[nH]n1 | HO- | C(CCC)O | null | null | COC(=O)C(C)n1cncn1.NN>C(CCC)O>CC(C(=O)NN)n1cncn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6db2cce419324c5cb504e5393ad45e68 | CCOC(=O)CBr.Oc1ncccc1Br>>CCOC(=O)Cn1cccc(Br)c1=O | CCCCCCC.BrC=1C(=NC=CC1)O.BrCC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(CN1C(C(=CC=C1)Br)=O)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[n:7]1[cH:8][cH:9][cH:10][c:11]([Br:12])[c:13]1[OH:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][cH:10][c:11]([Br:12])[c:13]1=[O:14] | CCOC(=O)CBr.Oc1ncccc1Br | CCOC(=O)Cn1cccc(Br)c1=O | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 6dfdbac002000b49828e22c4b69d4571a0c0c3202697b85b5a08225e6955028a | 5e9e0b01f8c9a1c10ac2bdfadca2d4bb3d9d0593654f2be0a33adb4d01012cf3 | O=c1cccc[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[Br;D1;H0:6]-[c:7]1:[c:8]:[c:9]:[c:10]:[n;H0;D2;+0:11]:[c;H0;D3;+0:12]:1-[OH;D1;+0:13]>>[Br;D1;H0:6]-[c:7]1:[c:8]:[c:9]:[c:10]:[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5]):[c;H0;D3;+0:12]:1=[O;H0;D1;+0:13] | 55 | [{"value": 55.0, "product": "C(C)OC(CN1C(C(=CC=C1)Br)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 320a, 3-bromo-2-hydroxy-pyridine was reacted with ethyl bromoacetate and potassium carbonate. Extractive workup followed by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50) afforded the title compound as a light yellow oil (yield: 55%), which was directly used in the next step.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | C(C)(=O)OCC | null | null | CCOC(=O)CBr.Oc1ncccc1Br>C(C)(=O)OCC>CCOC(=O)Cn1cccc(Br)c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-85bae26dc8f64b46b36b6910f0c0b0d1 | CCOC(=O)Cn1cccc(Br)c1=O.NN>>NNC(=O)Cn1cccc(Br)c1=O | C(C)OC(CN1C(C(=CC=C1)Br)=O)=O.O.NN>>BrC=1C(N(C=CC1)CC(=O)NN)=O | CCO[C:3](=[O:4])[CH2:5][n:6]1[cH:7][cH:8][cH:9][c:10]([Br:11])[c:12]1=[O:13].[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][n:6]1[cH:7][cH:8][cH:9][c:10]([Br:11])[c:12]1=[O:13] | CCOC(=O)Cn1cccc(Br)c1=O.NN | NNC(=O)Cn1cccc(Br)c1=O | null | null | C(CCC)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | O=c1cccc[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 62 | [{"value": 62.0, "product": "BrC=1C(N(C=CC1)CC(=O)NN)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (3-bromo-2-oxo-2H-pyridin-1-yl)-acetic acid ethyl ester in butanol was reacted with hydrazine hydrate (1.2 equivalents) at reflux for 16 h. The precipitate was filtered and triturated with hot methanol to afford the title compound as an off-white solid (yield: 62%). MS: m/e=244.2/246.2 [M... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccncc1 | HO- | C(CCC)O | null | null | CCOC(=O)Cn1cccc(Br)c1=O.NN>C(CCC)O>NNC(=O)Cn1cccc(Br)c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3aad6f459cfe4326ad8c19288ce80229 | CC1C=NNC1=O.CCOC(=O)CBr>>CCOC(=O)Cn1cc(C)c(=O)[nH]1 | CCCCCCC.CC1C=NNC1=O.BrCC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(CN1NC(C(=C1)C)=O)=O | [N:7]1=[CH:8][CH:9]([CH3:10])[C:11](=[O:12])[NH:13]1.Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][c:9]([CH3:10])[c:11](=[O:12])[nH:13]1 | CC1C=NNC1=O.CCOC(=O)CBr | CCOC(=O)Cn1cc(C)c(=O)[nH]1 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 20c101320b8ac86519a3347e507965089cbf375b3d82b6c2e7839bdb6c5ac378 | c7c13ec804ee909cea6287c19c05017bf2ccbeecbbfe7a5965d1d762a284c97f | O=c1cc[nH][nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C;D1;H3:6]-[CH;D3;+0:7]1-[CH;D2;+0:8]=[N;H0;D2;+0:9]-[NH;D2;+0:10]-[C;H0;D3;+0:11]-1=[O;D1;H0:12]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[cH;D2;+0:8]:[c;H0;D3;+0:7](-[C;D1;H3:6]):[c;H0;D3;+0:11](=[O;D1;H0:12]):[nH;D2;+0:10]:1 | 16 | [{"value": 16.0, "product": "C(C)OC(CN1NC(C(=C1)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 320a, 4-methyl-2-pyrazolin-5-one was reacted with ethyl bromoacetate and potassium carbonate. Extractive workup followed by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50) afforded the title compound as a white solid (yield: 16%). MS: m/e=185.0 [M+H]+.
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide.Primary halide.Ester | Ester | C1=NNCC1 | c1cn[nH]c1 | c1cn[nH]c1 | HBr | C(C)(=O)OCC | null | null | CC1C=NNC1=O.CCOC(=O)CBr>C(C)(=O)OCC>CCOC(=O)Cn1cc(C)c(=O)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-108e5e87af074ab59bf196fe349f8eac | COC(=O)C(O)C1CC1.NN>>NNC(=O)C(O)C1CC1 | COC(C(O)C1CC1)=O.O.NN>>C1(CC1)C(C(=O)NN)O | CO[C:3](=[O:4])[CH:5]([OH:6])[CH:7]1[CH2:8][CH2:9]1.[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH:5]([OH:6])[CH:7]1[CH2:8][CH2:9]1 | COC(=O)C(O)C1CC1.NN | NNC(=O)C(O)C1CC1 | null | null | CO | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | C1CC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[O;D1;H1:5].[N;D1;H2:6]-[NH2;D1;+0:7]>>[C:4]-[C:3](-[O;D1;H1:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[N;D1;H2:6] | 69 | [{"value": 69.0, "product": "C1(CC1)C(C(=O)NN)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (rac.)-2-cyclopropyl-2-hydroxy-acetic acid methyl ester (Newall, Christopher Earle; Foxton, Michael Walter; Hartley, Charles David; Looker, Brian Edgar. Cephalosporin antibiotics. Eur. Pat. Appl. (1985), 57 pp) in methanol was reacted with hydrazine hydrate (1.0 equivalent) at rt for 76 h... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | C1CC1 | HO- | CO | null | null | COC(=O)C(O)C1CC1.NN>CO>NNC(=O)C(O)C1CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18a74b86c985445bbe1810535f597593 | CCOC(=O)CN1CCOC1=O.NN>>NNC(=O)CN1CCOC1=O | C(C)OC(CN1C(OCC1)=O)=O.O.NN>>O=C1OCCN1CC(=O)NN | CCO[C:3](=[O:4])[CH2:5][N:6]1[CH2:7][CH2:8][O:9][C:10]1=[O:11].[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][N:6]1[CH2:7][CH2:8][O:9][C:10]1=[O:11] | CCOC(=O)CN1CCOC1=O.NN | NNC(=O)CN1CCOC1=O | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | O=C1NCCO1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7].[N;D1;H2:8]-[NH2;D1;+0:9]>>[#8:7]-[C:5](=[O;D1;H0:6])-[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[N;D1;H2:8] | 77 | [{"value": 77.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (2-oxo-oxazolidin-3-yl)-acetic acid ethyl ester (Potts, Kevin T.; Bhattacharjee, Debkumar; Kanemasa, Shuji. Journal of Organic Chemistry (1980), 45(24), 4985-8) in ethanol was reacted with hydrazine hydrate (1.0 equivalent) at rt for 72 h. All volatiles were evaporated, the residue was ch... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | C1COC[NH]1 | HO- | C(C)O | null | null | CCOC(=O)CN1CCOC1=O.NN>C(C)O>NNC(=O)CN1CCOC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-520232ade3bd4eb4b79877e21eb1d435 | O=C1CN2CCC1CC2>>C1CN2CCC1C1(CO1)C2 | O.[I-].C[S+](=O)(C)C.[H-].[Na+].N12CC(C(CC1)CC2)=O>>O1C2(C1)CN1CCC2CC1 | [CH2:1]1[CH2:2][N:3]2[CH2:4][CH2:5][CH:6]1[C:7](=[O:9])[CH2:10]2>>[CH2:1]1[CH2:2][N:3]2[CH2:4][CH2:5][CH:6]1[C:7]1([CH2:8][O:9]1)[CH2:10]2 | O=C1CN2CCC1CC2 | C1CN2CCC1C1(CO1)C2 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 1d2de7e8761d4ac43c89e1777f675ff6bbb77776d7762a997d103a4f39a2764f | 65a8af0997ec9f56fa44fac9e6db8d8aeec07e535d6b4d216a6180693919dc05 | C1CN2CCC1C1(CO1)C2 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[#7:4]2-[C:5]-[C:6]-[C:7]-1-[C:8]-[C:9]-2>>[C:3]1-[#7:4]2-[C:5]-[C:6]-[C:7](-[C:8]-[C:9]-2)-[C;H0;D4;+0:2]-12-[C:10]-[O;H0;D2;+0:1]-2 | 83.1 | [{"value": 83.0, "product": "O1C2(C1)CN1CCC2CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.1, "product": "O1C2(C1)CN1CCC2CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 67.5 | CELSIUS | 1 | HOUR | A mixture of trimethylsulfoxonium iodide (16.10 g, 73.2, mmol) and a dispersion of sodium hydride (60% in oil, 3.00 g, 75.0 mmol) in anhydrous dimethyl sulfoxide was stirred at room temperature under nitrogen for 30 minutes. Quinuclidin-3-one (7.05 g, 56.3 mmol) was then added as a solid portionwise, and the resulting ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ether | C1CN2CCC1CC2 | C1CN2CCC1C1(CO1)C2 | C1CN2CCC1C1(CO1)C2 | Other | CS(=O)C | 67.5 | 1 | O=C1CN2CCC1CC2>CS(=O)C>C1CN2CCC1C1(CO1)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ad948d750664b37908a63ff8f7e4490 | CC(=O)OC(C)(C)C.O=C1CN2CCC1CC2>>CC(C)(C)OC(=O)CC1(O)CN2CCC1CC2 | N12CC(C(CC1)CC2)=O.C(C)(=O)OC(C)(C)C.C(C)(C)NC(C)C.C(CCC)[Li]>>C(C)(C)(C)OC(CC1(CN2CCC1CC2)O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH3:8].[C:9]1(=[O:10])[CH2:11][N:12]2[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9]1([OH:10])[CH2:11][N:12]2[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]2 | CC(=O)OC(C)(C)C.O=C1CN2CCC1CC2 | CC(C)(C)OC(=O)CC1(O)CN2CCC1CC2 | null | null | O1CCCC1.O | C-C Coupling | OtherReaction | 94d6803c7d74b3309832e8415c4e91ad841bbe8c96cf64395c33ff657c37d792 | 044a18e4d3accc9215121cf8386364d4c22240176cddbc024e8f77ed5574d3a0 | C1CN2CCC1CC2 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](-[CH3;D1;+0:7])=[O;D1;H0:8].[O;H0;D1;+0:9]=[C;H0;D3;+0:10]1-[C:11]-[#7:12]2-[C:13]-[C:14]-[C:15]-1-[C:16]-[C:17]-2>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:8])-[CH2;D2;+0:7]-[C;H0;D4;+0:10]1(-[OH;D1;+0:9])-[C:11]-[#7:12]2-[C:13]-[C:... | null | [] | -78 | CELSIUS | 40 | MINUTE | To a solution of diisopropylamine (6.7 mL) in tetrahydrofuran (THF) (20 mL) at 0° C. was added n-butyllithium (2.3M in hexanes; 20 mL). The reaction mixture was stirred for 40 minutes and then cooled to −78° C. To this mixture a solution of t-butyl acetate (6.4 mL) in THF (10 mL) was added dropwise and stirring was con... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ester.Tertiary alcohol | C1CN2CCC1CC2 | C1CN2CCC1CC2 | C1CN2CCC1CC2 | null | O1CCCC1.O | -78 | 0.666667 | CC(=O)OC(C)(C)C.O=C1CN2CCC1CC2>O1CCCC1.O>CC(C)(C)OC(=O)CC1(O)CN2CCC1CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-580edcc21b3943089555aff97a359acc | CC(C)(C)OC(=O)CC1(O)CN2CCC1CC2>>COC(=O)CC1(O)CN2CCC1CC2 | FC(C(=O)O)(F)F.C(C)(C)(C)OC(CC1(CN2CCC1CC2)O)=O>>COC(CC1(CN2CCC1CC2)O)=O | C[C:1](C)(C)[O:2][C:3](=[O:4])[CH2:5][C:6]1([OH:7])[CH2:8][N:9]2[CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14]2>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]1([OH:7])[CH2:8][N:9]2[CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14]2 | CC(C)(C)OC(=O)CC1(O)CN2CCC1CC2 | COC(=O)CC1(O)CN2CCC1CC2 | null | null | ClCCl | Miscellaneous | OtherReaction | 65c8f61c086a235ce6692c51186a0187b2fa4d47add33293a3d7824255d1a4bf | 019584698d6f4e780dc33c58bbe427f505956c44d516240fec11049769c33a01 | C1CN2CCC1CC2 | C-[C;H0;D4;+0:1](-C)(-C)-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH3;D1;+0:1] | 48.6 | [{"value": 48.6, "product": "COC(CC1(CN2CCC1CC2)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Trifluoroacetic acid (40 mL) was added dropwise over 15 minutes to a solution of 2-(3-hydroxy-1-azabicyclo[2.2.2]oct-3-yl)acetic acid t-butyl ester (15.7 g) in anhydrous dichloromethane (40 mL) at 0° C. The mixture was stirred for 24 hours at room temperature, then the solvent was evaporated under reduced pressure. The... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Ester | null | null | C1CN2CCC1CC2 | Other | ClCCl | null | 24 | CC(C)(C)OC(=O)CC1(O)CN2CCC1CC2>ClCCl>COC(=O)CC1(O)CN2CCC1CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4aa0c519b2443368aaf9af2257110b9 | O=C1CN2CCC1CC2>>C=CC1(O)CN2CCC1CC2 | Cl.N12CC(C(CC1)CC2)=O.C(=C)[Mg]Br.[OH-].[Na+]>>C(=C)C1(CN2CCC1CC2)O | [C:3]1(=[O:4])[CH2:5][N:6]2[CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11]2>>[CH2:1]=[CH:2][C:3]1([OH:4])[CH2:5][N:6]2[CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11]2 | O=C1CN2CCC1CC2 | C=CC1(O)CN2CCC1CC2 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | f21ddbb27da853085157398477990264463ccc31727c7da86599b64d000ecee1 | 2ce956c609b76ee2dc626ad09e785d954b7df9a7379fec6f4a0d038e8e2d1b2b | C1CN2CCC1CC2 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[#7:4]2-[C:5]-[C:6]-[C:7]-1-[C:8]-[C:9]-2>>[C;D1;H2:10]=[C:11]-[C;H0;D4;+0:2]1(-[OH;D1;+0:1])-[C:3]-[#7:4]2-[C:5]-[C:6]-[C:7]-1-[C:8]-[C:9]-2 | 54 | [{"value": 54.0, "product": "C(=C)C1(CN2CCC1CC2)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Under an argon atmosphere, a solution of 3-quinuclidinone (1.25 g, 10 mmol) in anhydrous tetrahydrofuran (10 mL) was added over 15 minutes to a 1 M solution of vinylmagnesium bromide in tetrahydrofuran (20 mL, 20 mmol) at 0° C. to 5° C., stirred at room temperature for 24 hours, cooled to 0° C., and acidified to pH 1 w... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol.Vinyl | C1CN2CCC1CC2 | C1CN2CCC1CC2 | C1CN2CCC1CC2 | Other | O1CCCC1 | null | 24 | O=C1CN2CCC1CC2>O1CCCC1>C=CC1(O)CN2CCC1CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad0a923fc5134e3ead3d7adfab6b63fc | CI.Oc1ncccc1Br>>COc1ncccc1Br | BrC=1C(=NC=CC1)O.IC>>BrC=1C(=NC=CC1)OC | I[CH3:1].[OH:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[Br:9]>>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[Br:9] | CI.Oc1ncccc1Br | COc1ncccc1Br | null | C([O-])([O-])=O.[Ag+2] | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccncc1 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 62.5 | [{"value": 62.0, "product": "BrC=1C(=NC=CC1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.5, "product": "BrC=1C(=NC=CC1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Under an argon atmosphere, a mixture of 3-bromo-2-hydroxypyridine (3.49 g, 20 mmol), silver carbonate (3.67 g, 13.31 mmol), and iodomethane (1.5 mL, 24.1 mmol) in benzene (30 mL) was stirred in the dark at 40° C. to 50° C. for 24 hours, cooled in an ice bath, and filtered. The filtrate was washed once with 2% aqueous s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccncc1 | HI | C([O-])([O-])=O.[Ag+2].C1=CC=CC=C1 | null | 24 | CI.Oc1ncccc1Br>C([O-])([O-])=O.[Ag+2].C1=CC=CC=C1>COc1ncccc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eacd2701b2e144d580e592027d361c05 | BrBr.c1cnc2c(c1)CC1(CN3CCC1CC3)O2>>Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2 | C([O-])([O-])=O.[Na+].[Na+].O1C2(CC=3C1=NC=CC3)CN3CCC2CC3.C(C)(=O)[O-].[Na+].BrBr>>BrC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2 | Br[Br:1].[cH:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[CH2:8][C:9]1([CH2:10][N:11]3[CH2:12][CH2:13][CH:14]1[CH2:15][CH2:16]3)[O:17]2>>[Br:1][c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[CH2:8][C:9]1([CH2:10][N:11]3[CH2:12][CH2:13][CH:14]1[CH2:15][CH2:16]3)[O:17]2 | BrBr.c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | 52873c08474b84aeaea35f3c651ab8ce4e7921a0270815f2005959aaaae0cacf | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | Br-[Br;H0;D1;+0:1].[#8:2]-[c:3]1:[#7;a:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]:1>>[#8:2]-[c:3]1:[#7;a:4]:[c:5]:[c;H0;D3;+0:6](-[Br;H0;D1;+0:1]):[c:7]:[c:8]:1 | 81 | [{"value": 81.0, "product": "BrC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.1, "product": "BrC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (100 mg, 0.462 mmol) and sodium acetate (410 mg, 5 mmol) in 50% aqueous acetic acid (4 mL) was heated to 60° C. Bromine (0.100 mL, 1.94 mmol) was added via a syringe over 10 minutes, and the solution was then heated under reflux for 1 hour. Th... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | HBr | C(C)(=O)O | null | null | BrBr.c1cnc2c(c1)CC1(CN3CCC1CC3)O2>C(C)(=O)O>Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d25f2503cfbe47ee97e0b4ecb90838d9 | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2.OB(O)c1ccccc1>>c1ccc(-c2cnc3c(c2)CC2(CN4CCC2CC4)O3)cc1 | C([O-])([O-])=O.[Na+].[Na+].BrC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2.C1(=CC=CC=C1)B(O)O.COCCOC>>C1(=CC=CC=C1)C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2 | Br[c:5]1[cH:6][n:7][c:8]2[c:9]([cH:10]1)[CH2:11][C:12]1([CH2:13][N:14]3[CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19]3)[O:20]2.OB(O)[c:4]1[cH:3][cH:2][cH:1][cH:22][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][n:7][c:8]3[c:9]([cH:10]2)[CH2:11][C:12]2([CH2:13][N:14]4[CH2:15][CH2:16][CH:17]2[CH2:18][CH2:19]4)[O:20]3)[cH:21][... | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2.OB(O)c1ccccc1 | c1ccc(-c2cnc3c(c2)CC2(CN4CCC2CC4)O3)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C(C)O | C-C Coupling | Suzuki coupling with boronic acids | 5532cdf25c636ff194e1c9e6a6006682a2770fdb59d30b0bcbc1b23d8404c91e | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cnc3c(c2)CC2(CN4CCC2CC4)O3)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]:[c:6]:1)-[#8:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#8:7]-[c:4]1:[#7;a:5]:[c:6]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:2]:[c:3]:1 | 68.5 | [{"value": 68.0, "product": "C1(=CC=CC=C1)C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.5, "product": "C1(=CC=CC=C1)C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Under a nitrogen atmosphere, 5′-bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (118 mg, 0.4 mmol), phenylboronic acid (54 mg, 0.443 mmol), and tetrakis(triphenylphosphine)palladium(0) (11 mg, 2.3 mol %) were stirred in a solution of 1,2-dimethoxyethane (3 mL) and ethanol (0.75 mL) containing 2M aqu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1ccccc1.c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1ccccc1.c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)O | null | null | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2.OB(O)c1ccccc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)O>c1ccc(-c2cnc3c(c2)CC2(CN4CCC2CC4)O3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e2bcaeee572442e29ef44100865b22cc | O=[N+]([O-])O.c1cnc2c(c1)CC1(CN3CCC1CC3)O2>>O=[N+]([O-])c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | O1C2(CC=3C1=NC=CC3)CN3CCC2CC3.[N+](=O)(O)[O-].C([O-])([O-])=O.[Na+].[Na+]>>[N+](=O)([O-])C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2 | O[N+:2](=[O:1])[O-:3].[cH:4]1[cH:5][n:6][c:7]2[c:8]([cH:9]1)[CH2:10][C:11]1([CH2:12][N:13]3[CH2:14][CH2:15][CH:16]1[CH2:17][CH2:18]3)[O:19]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[c:8]([cH:9]1)[CH2:10][C:11]1([CH2:12][N:13]3[CH2:14][CH2:15][CH:16]1[CH2:17][CH2:18]3)[O:19]2 | O=[N+]([O-])O.c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | O=[N+]([O-])c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | dadd112342dc5b925b662cd59df7d6fbcfbe4ee80f945deaec3673160c268cd2 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[#8:4]-[c:5]1:[#7;a:6]:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]:1>>[#8:4]-[c:5]1:[#7;a:6]:[c:7]:[c;H0;D3;+0:8](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:9]:[c:10]:1 | 51 | [{"value": 51.0, "product": "[N+](=O)([O-])C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.0, "product": "[N+](=O)([O-])C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (325 mg, 1.5 mmol) and fuming nitric acid (0.27 mL, 5.74 mmol) in sulfuric acid (0.75 mL) was heated at 70° C. to 80° C. for 24 hours. The resulting viscous solution was poured onto 15 g of ice and basified to pH>10 with solid sodium carbonate.... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | HO- | S(O)(O)(=O)=O | null | null | O=[N+]([O-])O.c1cnc2c(c1)CC1(CN3CCC1CC3)O2>S(O)(O)(=O)=O>O=[N+]([O-])c1cnc2c(c1)CC1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-400e8640d6b147e2a244d50dc9215ce0 | O=[N+]([O-])O.c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2>>O=[N+]([O-])c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | C([O-])([O-])=O.[K+].[K+].[N+](=O)(O)[O-].O1[C@@]2(CC=3C1=NC=CC3)CN3CCC2CC3.O>>[N+](=O)([O-])C=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2 | O[N+:2](=[O:1])[O-:3].[cH:4]1[cH:5][n:6][c:7]2[c:8]([cH:9]1)[CH2:10][C@@:11]1([CH2:12][N:13]3[CH2:14][CH2:15][CH:16]1[CH2:17][CH2:18]3)[O:19]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[c:8]([cH:9]1)[CH2:10][C@@:11]1([CH2:12][N:13]3[CH2:14][CH2:15][CH:16]1[CH2:17][CH2:18]3)[O:19]2 | O=[N+]([O-])O.c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | O=[N+]([O-])c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | ca6cf43857203756cf55b7572ca5ed70b01ca7c9564230f2a416edb151d1eb5a | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[#8:4]-[c:5]1:[#7;a:6]:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]:1>>[#8:4]-[c:5]1:[#7;a:6]:[c:7]:[c;H0;D3;+0:8](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:9]:[c:10]:1 | 98.6 | [{"value": 98.0, "product": "[N+](=O)([O-])C=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.6, "product": "[N+](=O)([O-])C=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 67.5 | CELSIUS | 1 | HOUR | (R)-(−)-Spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (3.03 g, 14 mmol) was dissolved in concentrated sulfuric acid (7 mL) at 0-5 ° C., fuming nitric acid (3.3 mL, 70.2 mmol) was added over 10 minutes, the mixture was stirred for 1 hour, and heated at 65-70° C. for 24 hours. Cooled, poured onto ice (20... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | HO- | S(O)(O)(=O)=O | 67.5 | 1 | O=[N+]([O-])O.c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2>S(O)(O)(=O)=O>O=[N+]([O-])c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f99a1b3a022b433494a5dafe732c7480 | O=[N+]([O-])c1cnc2c(c1)CC1(CN3CCC1CC3)O2>>Nc1cnc2c(c1)CC1(CN3CCC1CC3)O2 | [N+](=O)([O-])C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2.[H][H]>>NC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2 | O=[N+:1]([O-])[c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[CH2:8][C:9]1([CH2:10][N:11]3[CH2:12][CH2:13][CH:14]1[CH2:15][CH2:16]3)[O:17]2>>[NH2:1][c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[CH2:8][C:9]1([CH2:10][N:11]3[CH2:12][CH2:13][CH:14]1[CH2:15][CH2:16]3)[O:17]2 | O=[N+]([O-])c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | Nc1cnc2c(c1)CC1(CN3CCC1CC3)O2 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]-[#8:7]>>[#8:7]-[c:6]:[#7;a:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 98 | [{"value": 98.0, "product": "NC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.9, "product": "NC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5′-nitrospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (1.4 g, 5.36 mmol), and 10% palladium on carbon (48% water wet, 270 mg) in methanol (90 mL) was hydrogenated for 1 hour at 50 psi of hydrogen. The catalyst was filtered off through a pad of celite and the solvent was evaporated under re... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | Other | [Pd].CO | null | null | O=[N+]([O-])c1cnc2c(c1)CC1(CN3CCC1CC3)O2>[Pd].CO>Nc1cnc2c(c1)CC1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2c93104eb5f94015a581ed27c197d6b4 | O=[N+]([O-])c1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2>>Nc1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2 | [N+](=O)([O-])C=1C=C2C(=NC1)O[C@]1(C2)CN2CCC1CC2>>NC=1C=C2C(=NC1)O[C@]1(C2)CN2CCC1CC2 | O=[N+:1]([O-])[c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[CH2:8][C@:9]1([CH2:10][N:11]3[CH2:12][CH2:13][CH:14]1[CH2:15][CH2:16]3)[O:17]2>>[NH2:1][c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[CH2:8][C@:9]1([CH2:10][N:11]3[CH2:12][CH2:13][CH:14]1[CH2:15][CH2:16]3)[O:17]2 | O=[N+]([O-])c1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2 | Nc1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2 | null | null | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]-[#8:7]>>[#8:7]-[c:6]:[#7;a:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 92 | [{"value": 92.0, "product": "NC=1C=C2C(=NC1)O[C@]1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.6, "product": "NC=1C=C2C(=NC1)O[C@]1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The enantiomer (S)-(+)-5′nitrospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (6.85 g, 26.2 mmol) treated in the same way as described in example 8A in ammoniated methanol provided the title compound (5.55 g, 24 mmol, 92%): electrospray MS (m/z, relative intensity) 232 ([MH]+, 100).
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2 | Other | CO | null | null | O=[N+]([O-])c1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2>CO>Nc1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4c4e218f34534cd1833e59d19281cd2d | Nc1cnc2c(c1)CC1(CN3CCC1CC3)O2.O=C=Nc1ccccc1>>O=C(Nc1ccccc1)Nc1cnc2c(c1)CC1(CN3CCC1CC3)O2 | C1(=CC=CC=C1)N=C=O.NC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2>>C1(=CC=CC=C1)NC(=O)NC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2 | [NH2:10][c:11]1[cH:12][n:13][c:14]2[c:15]([cH:16]1)[CH2:17][C:18]1([CH2:19][N:20]3[CH2:21][CH2:22][CH:23]1[CH2:24][CH2:25]3)[O:26]2.[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[NH:10][c:11]1[cH:12][n:13][c:14]2[c:15]([cH:16]1)[CH2:17][C:18]1([CH2:19][N... | Nc1cnc2c(c1)CC1(CN3CCC1CC3)O2.O=C=Nc1ccccc1 | O=C(Nc1ccccc1)Nc1cnc2c(c1)CC1(CN3CCC1CC3)O2 | null | null | O1CCCC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1cnc2c(c1)CC1(CN3CCC1CC3)O2 | [#8:1]-[c:2]:[#7;a:3]:[c:4]:[c:5](-[NH2;D1;+0:6]):[c:7].[O;D1;H0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#8:1]-[c:2]:[#7;a:3]:[c:4]:[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:9](=[O;D1;H0:8])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:7] | 86 | [{"value": 86.0, "product": "C1(=CC=CC=C1)NC(=O)NC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.0, "product": "C1(=CC=CC=C1)NC(=O)NC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | Under a nitrogen atmosphere, phenyl isocyanate (0.056 mL, 0.515 mmol) was added to a suspension of 5′-aminospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (119 mg, 0.514 mmol) in anhydrous tetrahydrofuran (5 mL) and stirred for 12 hours. The solvent was evaporated under reduced pressure and the residue p... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | null | O1CCCC1 | null | 12 | Nc1cnc2c(c1)CC1(CN3CCC1CC3)O2.O=C=Nc1ccccc1>O1CCCC1>O=C(Nc1ccccc1)Nc1cnc2c(c1)CC1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-340e8386b3ab433387d1baaaf25bcefb | C=O.Nc1cnc2c(c1)CC1(CN3CCC1CC3)O2>>CNc1cnc2c(c1)CC1(CN3CCC1CC3)O2 | [BH4-].[Na+].NC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2.C=O.[Na].[OH-].[K+]>>CNC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2 | O=[CH2:1].[NH2:2][c:3]1[cH:4][n:5][c:6]2[c:7]([cH:8]1)[CH2:9][C:10]1([CH2:11][N:12]3[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]3)[O:18]2>>[CH3:1][NH:2][c:3]1[cH:4][n:5][c:6]2[c:7]([cH:8]1)[CH2:9][C:10]1([CH2:11][N:12]3[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]3)[O:18]2 | C=O.Nc1cnc2c(c1)CC1(CN3CCC1CC3)O2 | CNc1cnc2c(c1)CC1(CN3CCC1CC3)O2 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive methylation of primary amine with formaldehyde | 51d235def9103cd7a524cbedb590276839772d481304df37a121e64cb81721f4 | cf32f1267c674fd84d46b8a676a46bd4e3a018dea282d34ea9ab93d79b66d0ee | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | O=[CH2;D1;+0:1].[#8:2]-[c:3]:[#7;a:4]:[c:5]:[c:6](-[NH2;D1;+0:7]):[c:8]>>[#8:2]-[c:3]:[#7;a:4]:[c:5]:[c:6](-[NH;D2;+0:7]-[CH3;D1;+0:1]):[c:8] | 64 | [{"value": 64.0, "product": "CNC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.0, "product": "CNC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 1 | HOUR | Under a nitrogen atmosphere, sodium (50 mg, 2.17 mmol) was slowly added (exothermic) to methanol (1 mL) and stirred for 1 hour. 5′-Aminospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (115 mg, 0.5 mmol) and paraformaldehyde (35 mg, 1.17 mmol) were added and stirred for 16 hours. The reaction was heated a... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Secondary amine | null | null | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | Other | CO | 50 | 1 | C=O.Nc1cnc2c(c1)CC1(CN3CCC1CC3)O2>CO>CNc1cnc2c(c1)CC1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-37fc548b8c7243d2b119e04116c1608c | Brc1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2.C=Cc1ccccc1>>C(=C/c1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2)\c1ccccc1 | BrC=1C=C2C(=NC1)O[C@]1(C2)CN2CCC1CC2.C=CC1=CC=CC=C1.C(C)N(CC)CC>>C1(=CC=CC=C1)/C=C/C=1C=C2C(=NC1)O[C@]1(C2)CN2CCC1CC2 | Br[c:3]1[cH:4][n:5][c:6]2[c:7]([cH:8]1)[CH2:9][C@:10]1([CH2:11][N:12]3[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]3)[O:18]2.[CH:1](=[CH2:2])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][n:5][c:6]2[c:7]([cH:8]1)[CH2:9][C@:10]1([CH2:11][N:12]3[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]3)[O:18]2)\[c:19... | Brc1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2.C=Cc1ccccc1 | C(=C/c1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2)\c1ccccc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C | C(C)#N | C-C Coupling | Heck terminal vinyl | e90651fdb05c01d851278e5ae382bcae6fa85b26ae953ac6a6c1431f21633399 | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | C(=C/c1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2)\c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[c:5]:[c:6]:1)-[#8:7].[CH2;D1;+0:8]=[C:9]-[c:10]>>[#8:7]-[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](/[CH;D2;+0:8]=[C:9]/[c:10]):[c:6]:[c:5]:1 | 55 | [{"value": 55.0, "product": "C1(=CC=CC=C1)/C=C/C=1C=C2C(=NC1)O[C@]1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.9, "product": "C1(=CC=CC=C1)/C=C/C=1C=C2C(=NC1)O[C@]1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A solution of (S)-(+)-5′-bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (150 mg, 0.51 mmol), styrene (0.07 mL, 0.61 mmol), palladium(II)acetate (1.2 mg, 0.0053 mmol), tri-o-tolylphosphine (6.4 mg, 0.021 mmol), and triethylamine (0.5 mL, 3.6 mmol) in anhydrous acetonitrile (0.5 mL), in a heavy-walle... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2 | c1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2 | c1ccccc1.c1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.C(C)#N | 100 | null | Brc1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2.C=Cc1ccccc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.C(C)#N>C(=C/c1cnc2c(c1)C[C@]1(CN3CCC1CC3)O2)\c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-81734a9017f04404bb22a1ceee0a0fbd | Brc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2.C1CNC1>>c1nc2c(cc1N1CCC1)C[C@@]1(CN3CCC1CC3)O2 | BrC=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2.N1CCC1.CC(C)([O-])C.[Na+].C1(=CC=CC=C1)P(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1>>N1(CCC1)C=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2 | Br[c:6]1[cH:1][n:2][c:3]2[c:4]([cH:5]1)[CH2:11][C@@:12]1([CH2:13][N:14]3[CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19]3)[O:20]2.[NH:7]1[CH2:8][CH2:9][CH2:10]1>>[cH:1]1[n:2][c:3]2[c:4]([cH:5][c:6]1[N:7]1[CH2:8][CH2:9][CH2:10]1)[CH2:11][C@@:12]1([CH2:13][N:14]3[CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19]3)[O:20]2 | Brc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2.C1CNC1 | c1nc2c(cc1N1CCC1)C[C@@]1(CN3CCC1CC3)O2 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O1CCCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 79956164f14638ce7279e5ff4e5a606cb458c293e21fea7c157a94bae280fe56 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1nc2c(cc1N1CCC1)C[C@@]1(CN3CCC1CC3)O2 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[c:5]:[c:6]:1)-[#8:7].[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[#8:7]-[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]2-[C:8]-[C:9]-[C:10]-2):[c:6]:[c:5]:1 | null | [] | 75 | CELSIUS | null | null | (R)-(−)-5′-Bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (295 mg, 1 mmol), azetidine (0.101 mL, 1.5 mmol), sodium tert-butoxide (135 mg, 1.4 mmol), tris(dibenzylideneacetone)dipalladium (46 mg, 0.05 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (62 mg, 0.1 mmol) and anhydrous tetrahydrofuran ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNC1.c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | C1C[NH]C1.c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | C1C[NH]C1.c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCCC1 | 75 | null | Brc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2.C1CNC1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCCC1>c1nc2c(cc1N1CCC1)C[C@@]1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bd16bf666c344fe7a484df657614c6e0 | Brc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2.C=Cc1ccccn1>>C(=Cc1ccccn1)c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | BrC=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2.C(=C)C1=NC=CC=C1>>N1=C(C=CC=C1)C=CC=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2 | Br[c:9]1[cH:10][n:11][c:12]2[c:13]([cH:14]1)[CH2:15][C@@:16]1([CH2:17][N:18]3[CH2:19][CH2:20][CH:21]1[CH2:22][CH2:23]3)[O:24]2.[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][n:8]1>>[CH:1](=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][n:8]1)[c:9]1[cH:10][n:11][c:12]2[c:13]([cH:14]1)[CH2:15][C@@:16]1([CH2:17][N:18]3[CH2:19][CH2:20... | Brc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2.C=Cc1ccccn1 | C(=Cc1ccccn1)c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | null | null | null | C-C Coupling | Heck terminal vinyl | 868a29dcbb570a003a58cecf20153dd613d7e538ecd2b4cdca32c2d878e458b9 | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | C(=Cc1ccccn1)c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[c:5]:[c:6]:1)-[#8:7].[#7;a:8]:[c:9]-[C:10]=[CH2;D1;+0:11]>>[#7;a:8]:[c:9]-[C:10]=[CH;D2;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[c:5]:[c:6]:1)-[#8:7] | 24 | [{"value": 23.0, "product": "N1=C(C=CC=C1)C=CC=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.0, "product": "N1=C(C=CC=C1)C=CC=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (R)-(−)-5′-Bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (150 mg, 0.5 mmol) was treated with 2-vinylpyridine (0.070 mL, 0.65 mmol) in the same way as described in example 16. Purification by flash chromatography through silica gel (eluting with ammoniated ether/methanol, 95:5 to 9:1), followed by ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | c1ccncc1.c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | HBr | null | null | null | Brc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2.C=Cc1ccccn1>>C(=Cc1ccccn1)c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-994c984101db47199f1323f5c8ec8cf2 | Brc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2.C#C[Si](C)(C)C>>C[Si](C)(C)C#Cc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | BrC=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2.C[Si](C)(C)C#C.C(C)N(CC)CC>>C[Si](C#CC=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2)(C)C | Br[c:7]1[cH:8][n:9][c:10]2[c:11]([cH:12]1)[CH2:13][C@@:14]1([CH2:15][N:16]3[CH2:17][CH2:18][CH:19]1[CH2:20][CH2:21]3)[O:22]2.[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[CH:6]>>[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][n:9][c:10]2[c:11]([cH:12]1)[CH2:13][C@@:14]1([CH2:15][N:16]3[CH2:17][CH2:18][CH:19]1[CH2:20][CH... | Brc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2.C#C[Si](C)(C)C | C[Si](C)(C)C#Cc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C(C)#N | C-C Coupling | Sonogashira alkyne_aryl halide | a3bd626b113853621b10067445273ac04b50534fbcc79a3a9cd99df3a91a853f | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]:[c:6]:1)-[#8:7].[C;D1;H3:8]-[#14:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C:12]#[CH;D1;+0:13]>>[#8:7]-[c:4]1:[#7;a:5]:[c:6]:[c;H0;D3;+0:1](-[C;H0;D2;+0:13]#[C:12]-[#14:9](-[C;D1;H3:8])(-[C;D1;H3:10])-[C;D1;H3:11]):[c:2]:[c:3]:1 | 90 | [{"value": 90.0, "product": "C[Si](C#CC=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.0, "product": "C[Si](C#CC=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | (R)-(−)-5′-Bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine](295 mg, 1 mmol), trimethylsilylacetylene (0.355 mL, 2.5 mmol), tetrakis(triphenylphosphine)palladium (230 mg, 0.2 mmol), triethylamine (2 mL) and anhydrous acetonitrile (2 mL) were combined in a heavy-walled threaded glass tube containing a ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | HBr | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)#N | 100 | null | Brc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2.C#C[Si](C)(C)C>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)#N>C[Si](C)(C)C#Cc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c05d78cea0d4b71b97f75b6203ea618 | C[Si](C)(C)C#Cc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2>>C#Cc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C[Si](C#CC=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2)(C)C>>C(#C)C=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2 | C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][n:5][c:6]2[c:7]([cH:8]1)[CH2:9][C@@:10]1([CH2:11][N:12]3[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]3)[O:18]2>>[CH:1]#[C:2][c:3]1[cH:4][n:5][c:6]2[c:7]([cH:8]1)[CH2:9][C@@:10]1([CH2:11][N:12]3[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]3)[O:18]2 | C[Si](C)(C)C#Cc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | C#Cc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | null | null | O1CCCC1 | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3]:[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]:[c:3]-[C:2]#[CH;D1;+0:1] | 59 | [{"value": 59.0, "product": "C(#C)C=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.8, "product": "C(#C)C=1C=C2C(=NC1)O[C@@]1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Under an argon atmosphere, a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (1.3 mL, 1.3 mmol) was added at 0° C. to a solution of (R)-(−)-5′-(2-trimethylsilylethynyl)spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (265 mg, 0.85 mmol) in anhydrous tetrahydrofuran (5 mL), and stirred at ro... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 | Other | O1CCCC1 | null | 2 | C[Si](C)(C)C#Cc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2>O1CCCC1>C#Cc1cnc2c(c1)C[C@@]1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7af79f3506d74c58ace3cefb3ebe7337 | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccco1>>c1coc(-c2cnc3c(c2)CC2(CN4CCC2CC4)O3)c1 | BrC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.[Cl-].[Li+].C(CCC)[Sn](C=1OC=CC1)(CCCC)CCCC>>O1C(=CC=C1)C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2 | Br[c:5]1[cH:6][n:7][c:8]2[c:9]([cH:10]1)[CH2:11][C:12]1([CH2:13][N:14]3[CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19]3)[O:20]2.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:4]1[o:3][cH:2][cH:1][cH:21]1>>[cH:1]1[cH:2][o:3][c:4](-[c:5]2[cH:6][n:7][c:8]3[c:9]([cH:10]2)[CH2:11][C:12]2([CH2:13][N:14]4[CH2:15][CH2:16][CH:17]2[CH2:18][CH2:19]... | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccco1 | c1coc(-c2cnc3c(c2)CC2(CN4CCC2CC4)O3)c1 | null | null | COCCOC.C(Cl)(Cl)Cl.CO | C-C Coupling | Stille reaction_aryl | cc39d7db0ec52886fc192130e358b3dc6844f4d8793ec13a4bc72377dc53431d | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1coc(-c2cnc3c(c2)CC2(CN4CCC2CC4)O3)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]:[c:6]:1)-[#8:7].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:8]1:[#8;a:9]:[c:10]:[c:11]:[c:12]:1>>[#8:7]-[c:4]1:[#7;a:5]:[c:6]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8]2:[#8;a:9]:[c:10]:[c:11]:[c:12]:2):[c:2]:[c:3]:1 | 89.2 | [{"value": 89.0, "product": "O1C(=CC=C1)C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.2, "product": "O1C(=CC=C1)C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution containing 5′-bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (103.5 mg, 0.351 mmol), tris(dibenzylidineacetone)dipalladium (0) (14 mg, 0.015 mmol), tri(o-tolyl)phosphine (44.4 mg, 0.146 mmol), lithium chloride (62 mg, 1.46 mmol), and 2-(tri-n-butylstannyl)furan (0.17 g, 0.476 mmol) in 1,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccoc1.c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1ccoc1.c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1ccoc1.c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | HBr.Sn | COCCOC.C(Cl)(Cl)Cl.CO | null | null | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccco1>COCCOC.C(Cl)(Cl)Cl.CO>c1coc(-c2cnc3c(c2)CC2(CN4CCC2CC4)O3)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1847636ca46e4936ac9734d1a061a8c8 | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccnc1>>c1cncc(-c2cnc3c(c2)CC2(CN4CCC2CC4)O3)c1 | BrC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.[Cl-].[Li+].C(CCC)[Sn](C=1C=NC=CC1)(CCCC)CCCC>>N1=CC(=CC=C1)C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2 | Br[c:6]1[cH:7][n:8][c:9]2[c:10]([cH:11]1)[CH2:12][C:13]1([CH2:14][N:15]3[CH2:16][CH2:17][CH:18]1[CH2:19][CH2:20]3)[O:21]2.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:5]1[cH:4][n:3][cH:2][cH:1][cH:22]1>>[cH:1]1[cH:2][n:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]3[c:10]([cH:11]2)[CH2:12][C:13]2([CH2:14][N:15]4[CH2:16][CH2:17][CH:18]2[C... | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccnc1 | c1cncc(-c2cnc3c(c2)CC2(CN4CCC2CC4)O3)c1 | null | null | COCCOC.C(Cl)(Cl)Cl.CO | C-C Coupling | Stille reaction_aryl | 37d69164b75540068270b99151e8df9b79907e3444ec6d2ae6d0930ed34f1bc1 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1cncc(-c2cnc3c(c2)CC2(CN4CCC2CC4)O3)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]:[c:6]:1)-[#8:7].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1>>[#8:7]-[c:4]1:[#7;a:5]:[c:6]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:2):[c:2]:[c:3]:1 | 37 | [{"value": 37.0, "product": "N1=CC(=CC=C1)C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.0, "product": "N1=CC(=CC=C1)C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution containing 5′-bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (158 mg, 0.535 mmol), tris(dibenzylidineacetone)dipalladium (0) (23 mg, 0.025 mmol), tri(o-tolyl)phosphine (66 mg, 0.217 mmol), lithium chloride (99 mg, 2.34 mmol), and 3-(tri-n-butylstannyl)pyridine (0.3 ml, approx. 0.3 g, app... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccncc1.c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1ccncc1.c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1ccncc1.c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | HBr.Sn | COCCOC.C(Cl)(Cl)Cl.CO | null | null | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccnc1>COCCOC.C(Cl)(Cl)Cl.CO>c1cncc(-c2cnc3c(c2)CC2(CN4CCC2CC4)O3)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ada3d4d6b6934258b1891af4fddb420f | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2.Cc1ccccc1P(c1ccccc1C)c1ccccc1C>>Cc1cnc2c(c1)CC1(CN3CCC1CC3)O2 | BrC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.[Cl-].[Li+].C[Sn](C)(C)C.C[Sn](C)(C)C>>CC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2 | Br[c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[CH2:8][C:9]1([CH2:10][N:11]3[CH2:12][CH2:13][CH:14]1[CH2:15][CH2:16]3)[O:17]2.Cc1ccccc1P(c1ccccc1C)c1ccccc1[CH3:1]>>[CH3:1][c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[CH2:8][C:9]1([CH2:10][N:11]3[CH2:12][CH2:13][CH:14]1[CH2:15][CH2:16]3)[O:17]2 | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2.Cc1ccccc1P(c1ccccc1C)c1ccccc1C | Cc1cnc2c(c1)CC1(CN3CCC1CC3)O2 | null | null | CO.C(Cl)(Cl)Cl.COCCOCCOC | C-C Coupling | OtherReaction | 006565e49c0251a32cb6e6adc643d7bcb3c08db70c255989d4adce0b2a1b79df | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[c:5]:[c:6]:1)-[#8:7].C-c1:c:c:c:c:c:1-P(-c1:c:c:c:c:c:1-C)-c1:c:c:c:c:c:1-[CH3;D1;+0:8]>>[#8:7]-[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[CH3;D1;+0:8]):[c:6]:[c:5]:1 | 166.3 | [{"value": 76.0, "product": "CC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 166.3, "product": "CC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 8 | HOUR | A solution containing 5′-bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (203 mg, 0.687 mmol), tris(dibenzylidineacetone)dipalladium (0) (33 mg, 0.036 mmol), tri(o-tolyl)phosphine (95 mg, 0.312 mmol), lithium chloride (241 mg, 5.69 mmol), and tetramethylstannane (1.0 ml, 1.3 g, 7.2 mmol) in 2-methox... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | HBr | CO.C(Cl)(Cl)Cl.COCCOCCOC | 100 | 8 | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2.Cc1ccccc1P(c1ccccc1C)c1ccccc1C>CO.C(Cl)(Cl)Cl.COCCOCCOC>Cc1cnc2c(c1)CC1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a4b5e2828164a48ac13b004ae0534ec | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2.CCCC[C]([SnH3])=C(CCCC)CCCC>>C=Cc1cnc2c(c1)CC1(CN3CCC1CC3)O2 | BrC=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.[Cl-].[Li+].C(CCC)C(=C(CCCC)CCCC)[SnH3]>>C(=C)C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2 | Br[c:3]1[cH:4][n:5][c:6]2[c:7]([cH:8]1)[CH2:9][C:10]1([CH2:11][N:12]3[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]3)[O:18]2.CCCC[C]([SnH3])=[C:2](CCCC)[CH2:1]CCC>>[CH2:1]=[CH:2][c:3]1[cH:4][n:5][c:6]2[c:7]([cH:8]1)[CH2:9][C:10]1([CH2:11][N:12]3[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]3)[O:18]2 | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2.CCCC[C]([SnH3])=C(CCCC)CCCC | C=Cc1cnc2c(c1)CC1(CN3CCC1CC3)O2 | null | null | COCCOC.C(Cl)(Cl)Cl.CO | C-C Coupling | OtherReaction | 18080a2f1bb3314985615348d358829f9d42deedef4105110c4aedd5fe47078a | 345410b3017f34cc8d6f132ba8118ca6d91a18aa6891eed5be0d88d66e3cb480 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[c:5]:[c:6]:1)-[#8:7].C-C-C-C-[C;H0;D3;+0:8](-[CH2;D2;+0:9]-C-C-C)=[C](-[SnH3])-C-C-C-C>>[#8:7]-[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[CH;D2;+0:8]=[CH2;D1;+0:9]):[c:6]:[c:5]:1 | 186.9 | [{"value": 76.0, "product": "C(=C)C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 186.9, "product": "C(=C)C=1C=C2C(=NC1)OC1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution containing 5′-bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (150 mg, 0.508 mmol), tris(dibenzylidineacetone)dipalladium (0) (22 mg, 0.024 mmol), tri(o-tolyl)phosphine (63 mg, 0.206 mmol), lithium chloride (103 mg, 2.43 mmol), and tri-n-butylvinylstannane (188 mg, 0.592 mmol) in 1,2-dime... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | Vinyl | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | HBr.Sn | COCCOC.C(Cl)(Cl)Cl.CO | null | null | Brc1cnc2c(c1)CC1(CN3CCC1CC3)O2.CCCC[C]([SnH3])=C(CCCC)CCCC>COCCOC.C(Cl)(Cl)Cl.CO>C=Cc1cnc2c(c1)CC1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-476390281feb45989a75873b005c2238 | Clc1nccc2c1CC1(CN3CCC1CC3)O2>>c1cc2c(cn1)CC1(CN3CCC1CC3)O2 | ClC1=NC=CC2=C1CC1(O2)CN2CCC1CC2>>O1C2(CC=3C=NC=CC31)CN3CCC2CC3 | Cl[c:5]1[c:4]2[c:3]([cH:2][cH:1][n:6]1)[O:16][C:8]1([CH2:7]2)[CH2:9][N:10]2[CH2:11][CH2:12][CH:13]1[CH2:14][CH2:15]2>>[cH:1]1[cH:2][c:3]2[c:4]([cH:5][n:6]1)[CH2:7][C:8]1([CH2:9][N:10]3[CH2:11][CH2:12][CH:13]1[CH2:14][CH2:15]3)[O:16]2 | Clc1nccc2c1CC1(CN3CCC1CC3)O2 | c1cc2c(cn1)CC1(CN3CCC1CC3)O2 | null | [Pd] | CO | Functional Group Interconversion | Aromatic dehalogenation | 409aba9ea2f495f1cd7575e2525e8cdbab4e3d3dad539182b1a11a900dffed41 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1cc2c(cn1)CC1(CN3CCC1CC3)O2 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]-[#8:6])-[C:7]>>[#8:6]-[c:5]:[c:4](:[cH;D2;+0:1]:[#7;a:2]:[c:3])-[C:7] | 104 | [{"value": 104.0, "product": "O1C2(CC=3C=NC=CC31)CN3CCC2CC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.4, "product": "O1C2(CC=3C=NC=CC31)CN3CCC2CC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | The 4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[3,2-c]pyridine] (125 mg or 5.0 mmol) from Example 33 was dissolved in 50 mL of anhydrous methanol, and 25 mg of 10% palladium on carbon was added. The bottle was placed on the Parr apparatus under hydrogen atmosphere and shaken for 2.5 hours. The Pd/C was remo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc2c(cn1)CC1(CN3CCC1CC3)O2 | c1cc2c(cn1)CC1(CN3CCC1CC3)O2 | c1cc2c(cn1)CC1(CN3CCC1CC3)O2 | Other | [Pd].CO | null | 2.5 | Clc1nccc2c1CC1(CN3CCC1CC3)O2>[Pd].CO>c1cc2c(cn1)CC1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36d6a0a3283b4c0cb8f1f21643e43c32 | Clc1ccnc2c1CC1(CN3CCC1CC3)O2.Sc1ccccc1>>c1ccc(Sc2ccnc3c2CC2(CN4CCC2CC4)O3)cc1 | [H-].[Na+].ClC1=C2C(=NC=C1)OC1(C2)CN2CCC1CC2.C1(=CC=CC=C1)S.CO>>C1(=CC=CC=C1)SC1=C2C(=NC=C1)OC1(C2)CN2CCC1CC2 | Cl[c:6]1[cH:7][cH:8][n:9][c:10]2[c:11]1[CH2:12][C:13]1([CH2:14][N:15]3[CH2:16][CH2:17][CH:18]1[CH2:19][CH2:20]3)[O:21]2.[cH:1]1[cH:2][cH:3][c:4]([SH:5])[cH:22][cH:23]1>>[cH:1]1[cH:2][cH:3][c:4]([S:5][c:6]2[cH:7][cH:8][n:9][c:10]3[c:11]2[CH2:12][C:13]2([CH2:14][N:15]4[CH2:16][CH2:17][CH:18]2[CH2:19][CH2:20]4)[O:21]3)[cH... | Clc1ccnc2c1CC1(CN3CCC1CC3)O2.Sc1ccccc1 | c1ccc(Sc2ccnc3c2CC2(CN4CCC2CC4)O3)cc1 | null | null | O1CCOCC1.O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution thiol | 4949d34a9b56fb58474d00eaedcaaefb0306d9d3b82d928dbda60c51edd0c176 | 97e4acce9b485bd597e518526ab4e9623782b1c9043b6e30dd257d386e3e5b01 | c1ccc(Sc2ccnc3c2CC2(CN4CCC2CC4)O3)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]:1-[C:7])-[#8:8].[SH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[#8:8]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[S;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:6]:1-[C:7] | 52 | [{"value": 52.0, "product": "C1(=CC=CC=C1)SC1=C2C(=NC=C1)OC1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.8, "product": "C1(=CC=CC=C1)SC1=C2C(=NC=C1)OC1(C2)CN2CCC1CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium hydride (151 mg, 3.77 mmol) was added to a solution of 97 mg (0.387 mmol) of 4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine], 0.40 mL (3.91 mmol) of thiophenol and 0.10 mL of methanol in 15 mL of dioxane, under a nitrogen atmosphere. The reaction was refluxed for 4 days, cooled to ambient... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic thiol | Monosulfide | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1ccccc1.c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | HCl | O1CCOCC1.O | null | null | Clc1ccnc2c1CC1(CN3CCC1CC3)O2.Sc1ccccc1>O1CCOCC1.O>c1ccc(Sc2ccnc3c2CC2(CN4CCC2CC4)O3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72df2477f6824919b7517ebb41e06fbc | Clc1ccnc2c1CC1(CN3CCC1CC3)O2.NCCN>>NCCNc1ccnc2c1CC1(CN3CCC1CC3)O2 | ClC1=C2C(=NC=C1)OC1(C2)CN2CCC1CC2.C(CN)N>>NCCNC1=C2C(=NC=C1)OC1(C2)CN2CCC1CC2 | Cl[c:5]1[cH:6][cH:7][n:8][c:9]2[c:10]1[CH2:11][C:12]1([CH2:13][N:14]3[CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19]3)[O:20]2.[NH2:1][CH2:2][CH2:3][NH2:4]>>[NH2:1][CH2:2][CH2:3][NH:4][c:5]1[cH:6][cH:7][n:8][c:9]2[c:10]1[CH2:11][C:12]1([CH2:13][N:14]3[CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19]3)[O:20]2 | Clc1ccnc2c1CC1(CN3CCC1CC3)O2.NCCN | NCCNc1ccnc2c1CC1(CN3CCC1CC3)O2 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 134857cf068afab7db9d749865c145d72b51c63b5036fd443b040ea288986bd5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]:1-[C:7])-[#8:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[#8:8]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[C:10]-[C:9]):[c:6]:1-[C:7] | null | [] | null | null | 4 | DAY | A solution of 74 mg (0.295 mmol) of 4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] in 10 mL of ethylenediamine was heated to reflux under a nitrogen atmosphere and stirred for 4 days. Upon cooling to ambient temperature, the solvent was removed in vacuo. The residue was dissolved in 20 mL of sa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | HCl | null | null | 96 | Clc1ccnc2c1CC1(CN3CCC1CC3)O2.NCCN>>NCCNc1ccnc2c1CC1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-80bc069d916e4770895774d36f8b9ca7 | Clc1ccnc2c1CC1(CN3CCC1CC3)O2.NCc1ccccc1>>c1ccc(CNc2ccnc3c2CC2(CN4CCC2CC4)O3)cc1 | ClC1=C2C(=NC=C1)OC1(C2)CN2CCC1CC2.C(C1=CC=CC=C1)N.C([O-])([O-])=O.[Na+].[Na+]>>C1(=CC=CC=C1)CNC1=C2C(=NC=C1)OC1(C2)CN2CCC1CC2 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]2[c:12]1[CH2:13][C:14]1([CH2:15][N:16]3[CH2:17][CH2:18][CH:19]1[CH2:20][CH2:21]3)[O:22]2.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:23][cH:24]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][n:10][c:11]3[c:12]2[CH2:13][C:14]2([CH2:15][N:16]4[CH2:17][CH2:18][CH:19]2[CH2:20][CH... | Clc1ccnc2c1CC1(CN3CCC1CC3)O2.NCc1ccccc1 | c1ccc(CNc2ccnc3c2CC2(CN4CCC2CC4)O3)cc1 | null | null | O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 134857cf068afab7db9d749865c145d72b51c63b5036fd443b040ea288986bd5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc3c2CC2(CN4CCC2CC4)O3)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]:1-[C:7])-[#8:8].[NH2;D1;+0:9]-[C:10]-[c:11]>>[#8:8]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:10]-[c:11]):[c:6]:1-[C:7] | 34 | [{"value": 34.0, "product": "C1(=CC=CC=C1)CNC1=C2C(=NC=C1)OC1(C2)CN2CCC1CC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of 97 mg (0.387 mmol) of 4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] in 5 mL of benzylamine was heated to reflux under a nitrogen atmosphere and stirred for 18 hours. Upon cooling to ambient temperature, the diluted with 40 mL of water, basicified with 2 mL of saturated aqueous so... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1ccccc1.c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | HCl | O | null | 18 | Clc1ccnc2c1CC1(CN3CCC1CC3)O2.NCc1ccccc1>O>c1ccc(CNc2ccnc3c2CC2(CN4CCC2CC4)O3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bf751cda76f642388b220e1284545732 | CN.Clc1ccnc2c1CC1(CN3CCC1CC3)O2>>CNc1ccnc2c1CC1(CN3CCC1CC3)O2 | ClC1=C2C(=NC=C1)OC1(C2)CN2CCC1CC2.CN>>CNC1=C2C(=NC=C1)OC1(C2)CN2CCC1CC2 | [CH3:1][NH2:2].Cl[c:3]1[cH:4][cH:5][n:6][c:7]2[c:8]1[CH2:9][C:10]1([CH2:11][N:12]3[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]3)[O:18]2>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][n:6][c:7]2[c:8]1[CH2:9][C:10]1([CH2:11][N:12]3[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]3)[O:18]2 | CN.Clc1ccnc2c1CC1(CN3CCC1CC3)O2 | CNc1ccnc2c1CC1(CN3CCC1CC3)O2 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 134857cf068afab7db9d749865c145d72b51c63b5036fd443b040ea288986bd5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]:1-[C:7])-[#8:8].[C;D1;H3:9]-[NH2;D1;+0:10]>>[#8:8]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[C;D1;H3:9]):[c:6]:1-[C:7] | null | [] | null | null | 8 | HOUR | A solution of 151 mg (0.60 mmol) of 4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] in 25 mL of 40% aqueous methylamine was heated to 175° C. in a steel bomb for 18 hours, then cooled to ambient temperature and concentrated in vacuo. The residue was dissolved in 10 mL of ethanol containing 0.4 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | c1cnc2c(c1)CC1(CN3CCC1CC3)O2 | HCl | null | null | 8 | CN.Clc1ccnc2c1CC1(CN3CCC1CC3)O2>>CNc1ccnc2c1CC1(CN3CCC1CC3)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-519cad054db84e83af78a0efbeb0aa4f | CC(C)(C)OC(=O)[C@@H]1C[C@@H](Oc2ccc(Cl)c3c2C2(CCCCC2)NC(=O)N3)C1.O>>CC(=O)O.O=C1Nc2c(Cl)ccc(O[C@@H]3C[C@@H](C(=O)O)C3)c2C2(CCCCC2)N1 | C(C)(C)(C)OC(=O)[C@@H]1C[C@H](C1)OC1=C2C3(NC(NC2=C(C=C1)Cl)=O)CCCCC3.Br.O>>C(C)(=O)O.ClC=1C=CC(=C2C3(NC(NC12)=O)CCCCC3)O[C@@H]3C[C@H](C3)C(=O)O | C[C:2](C)([CH3:1])[O:20][C:18]([C@H:17]1[CH2:16][C@H:15]([O:14][c:13]2[cH:12][cH:11][c:9]([Cl:10])[c:8]3[c:22]2[C:23]2([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[NH:29][C:6](=[O:5])[NH:7]3)[CH2:21]1)=[O:19].[OH2:3]>>[CH3:1][C:2](=[O:3])[OH:4].[O:5]=[C:6]1[NH:7][c:8]2[c:9]([Cl:10])[cH:11][cH:12][c:13]([O:14][C@H:15]3[CH... | CC(C)(C)OC(=O)[C@@H]1C[C@@H](Oc2ccc(Cl)c3c2C2(CCCCC2)NC(=O)N3)C1.O | CC(=O)O.O=C1Nc2c(Cl)ccc(O[C@@H]3C[C@@H](C(=O)O)C3)c2C2(CCCCC2)N1 | null | null | C(C)(=O)O | Acylation | OtherReaction | c226912d3365eb5e64be0dac8784ffb753b865db0f0adba41564a4f98ca8828d | c129c2d4bf8d003b6d5cd4342bab040c800a372eb4262218bb5ae9fce91f728a | O=C1Nc2cccc(OC3CCC3)c2C2(CCCCC2)N1 | C-[C;H0;D4;+0:1](-C)(-[C;D1;H3:2])-[O;H0;D2;+0:3]-[C:4](-[C:5])=[O;D1;H0:6].[OH2;D0;+0:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](-[O;D1;H1:8])=[O;H0;D1;+0:7].[C:5]-[C:4](=[O;D1;H0:6])-[OH;D1;+0:3] | null | [] | 60 | CELSIUS | 30 | MINUTE | The product of step (a) (207 g, 0.492 mol) was slurried in acetic acid (3100 ml) and heated to 60° C. 48% Hydrobromic acid (4.93 mol) was added dropwise keeping the temperature at 60° C. The solution was stirred at 60° C. for 30 minutes. Water (700 ml) was added dropwise keeping the temperature above 55° C. The slurry ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid.Carboxylic acid | null | null | C1CCC1.c1ccc2c(c1)NCNC21CCCCC1 | Other | C(C)(=O)O | 60 | 0.5 | CC(C)(C)OC(=O)[C@@H]1C[C@@H](Oc2ccc(Cl)c3c2C2(CCCCC2)NC(=O)N3)C1.O>C(C)(=O)O>CC(=O)O.O=C1Nc2c(Cl)ccc(O[C@@H]3C[C@@H](C(=O)O)C3)c2C2(CCCCC2)N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d7985848d23b4f51ade2ab9ba36c2753 | C=CCOCc1ccccc1.O=C(Cl)C(Cl)(Cl)Cl>>O=C1CC(COCc2ccccc2)C1(Cl)Cl | COCCOC.C(C1=CC=CC=C1)OCC=C.ClC(C(=O)Cl)(Cl)Cl.COCCOC>>C(C1=CC=CC=C1)OCC1C(C(C1)=O)(Cl)Cl | [CH2:3]=[CH:4][CH2:5][O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.Cl[C:2](=[O:1])[C:14](Cl)([Cl:15])[Cl:16]>>[O:1]=[C:2]1[CH2:3][CH:4]([CH2:5][O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[C:14]1([Cl:15])[Cl:16] | C=CCOCc1ccccc1.O=C(Cl)C(Cl)(Cl)Cl | O=C1CC(COCc2ccccc2)C1(Cl)Cl | null | [Zn].S(=O)(=O)([O-])[O-].[Cu+2] | O.C(C)OCC | C-C Coupling | OtherReaction | 6abbed25a72e027e758a3223966873406862851af82e412acd5d1f8b8bf66b2e | 57d4700a378a1cafce563da9f5eedffe4be9c91366df44aa034da7d71823d308 | O=C1CC(COCc2ccccc2)C1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3](-Cl)(-[Cl;D1;H0:4])-[Cl;D1;H0:5].[#8:6]-[C:7]-[CH;D2;+0:8]=[CH2;D1;+0:9]>>[#8:6]-[C:7]-[CH;D3;+0:8]1-[CH2;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3]-1(-[Cl;D1;H0:4])-[Cl;D1;H0:5] | 91 | [{"value": 91.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.0, "product": null, "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Zinc dust (6.54 g, 0.1 mol) was suspended in water (30 ml) and argon bubbled through the suspension for 15 minutes before the addition of copper (II) sulphate (780 mg, 3.1 mmol). The reaction mixture was stirred at room temperature, under argon for 30 minutes. The mixture was filtered under a stream of argon and the so... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trichloro group.Allyl | Tertiary halide.Tertiary halide.Ketone | null | C1CCC1 | C1CCC1.c1ccccc1 | Other | [Zn].S(=O)(=O)([O-])[O-].[Cu+2].O.C(C)OCC | null | 0.5 | C=CCOCc1ccccc1.O=C(Cl)C(Cl)(Cl)Cl>[Zn].S(=O)(=O)([O-])[O-].[Cu+2].O.C(C)OCC>O=C1CC(COCc2ccccc2)C1(Cl)Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e1b73198fb504a57abdf39bd7fa3a0f2 | O=C(n1ccnc1)n1ccnc1.OCc1ccccc1>>C=C1CC(C(=O)OCc2ccccc2)C1 | C(=O)(N1C=NC=C1)N1C=NC=C1.C(C1=CC=CC=C1)O>>C(C1=CC=CC=C1)OC(=O)C1CC(C1)=C | c1n[cH:2][cH:1]n1[C:5](n1[cH:3]n[cH:15][cH:4]1)=[O:6].[OH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH2:1]=[C:2]1[CH2:3][CH:4]([C:5](=[O:6])[O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1 | O=C(n1ccnc1)n1ccnc1.OCc1ccccc1 | C=C1CC(C(=O)OCc2ccccc2)C1 | null | null | C(C)(=O)OCC.C(C)OCC | Acylation | OtherReaction | 0903b1780b1860613067b6a279fd787affc985e3bf5d11f9fd80b72f9028cbc9 | 88e97d733db5d6c9928ade3a394c136a01dda34d71b6a4f75cbc78ddb2d31fc0 | C=C1CC(C(=O)OCc2ccccc2)C1 | [O;D1;H0:1]=[C;H0;D3;+0:2](-n1:[cH;D2;+0:3]:n:[cH;D2;+0:4]:[cH;D2;+0:5]:1)-n1:[cH;D2;+0:6]:[cH;D2;+0:7]:n:c:1.[OH;D1;+0:8]-[C:9]-[c:10]>>[CH2;D1;+0:6]=[C;H0;D3;+0:7]1-[CH2;D2;+0:4]-[CH;D3;+0:5](-[C;H0;D3;+0:2](=[O;D1;H0:1])-[O;H0;D2;+0:8]-[C:9]-[c:10])-[CH2;D2;+0:3]-1 | 115.2 | [{"value": 69.0, "product": "C(C1=CC=CC=C1)OC(=O)C1CC(C1)=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 115.2, "product": "C(C1=CC=CC=C1)OC(=O)C1CC(C1)=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A suspension of 1,1′-carbonyldiimidazole (1.59 g, 9.81 mmol) in ethyl acetate (5 ml) was added in portions to a solution of the product of Preparation 12 (1 g, 8.9 mmol) in ethyl acetate (5 ml). Gentle effervescence was observed. The mixture was stirred at room temperature for about 1.5 hours, benzyl alcohol (1.11 ml, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Ester.Vinyl | c1c[nH]cn1.c1c[nH]cn1 | C1CCC1 | C1CCC1.c1ccccc1 | Other | C(C)(=O)OCC.C(C)OCC | null | 1.5 | O=C(n1ccnc1)n1ccnc1.OCc1ccccc1>C(C)(=O)OCC.C(C)OCC>C=C1CC(C(=O)OCc2ccccc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ef08f14722d41c18085c414992dcd0f | COC(=O)C1(C(=O)OC)CCC1>>COC(=O)C1(CO)CCC1 | COC(=O)C1(CCC1)C(=O)OC.[H-].C(C)(C)(C)O[Al](OC(C)(C)C)OC(C)(C)C.[Li+]>>COC(=O)C1(CCC1)CO | CO[C:6]([C:5]1([C:3]([O:2][CH3:1])=[O:4])[CH2:8][CH2:9][CH2:10]1)=[O:7]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH2:6][OH:7])[CH2:8][CH2:9][CH2:10]1 | COC(=O)C1(C(=O)OC)CCC1 | COC(=O)C1(CO)CCC1 | null | null | O1CCCC1.[Cl-].[NH4+] | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CCC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7])(-[C:8])-[C:9]>>[C:8]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])(-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7])-[C:9] | 107.6 | [{"value": 107.6, "product": "COC(=O)C1(CCC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of 1,1-cyclobutanedicarboxylic acid dimethyl ester (available from Lancaster Synthesis Ltd, UK) (2.0 g, 11.6 mmol) in tetrahydrofuran (20 ml) at room temperature was added lithium tri-tert-butoxyaluminium hydride (25.5 ml of a 1M solution in tetrahydrofuran, 25.5 mmol) dropwise over 10 minutes. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CCC1 | Other | O1CCCC1.[Cl-].[NH4+] | null | 18 | COC(=O)C1(C(=O)OC)CCC1>O1CCCC1.[Cl-].[NH4+]>COC(=O)C1(CO)CCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-720b28c5db0f4890a338ebe8e375c616 | COc1ccc(Cl)c(N)c1.N#C[O-]>>COc1ccc(Cl)c(NC(N)=O)c1 | Cl.ClC1=C(N)C=C(C=C1)OC.C(C)(=O)O.[O-]C#N.[K+]>>ClC1=C(C=C(C=C1)OC)NC(=O)N | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[c:8]([NH2:9])[cH:13]1.[C:10](#[N:11])[O-:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[c:8]([NH:9][C:10]([NH2:11])=[O:12])[cH:13]1 | COc1ccc(Cl)c(N)c1.N#C[O-] | COc1ccc(Cl)c(NC(N)=O)c1 | null | null | O | Acylation | OtherReaction | f8798d1193af6f9b314ac8855e814716b90ff3758bcfa29778cc632fcaa83b7a | 5efe06db19c806d9e9798893351dc14c0cc48f1e8f8c857f54c6171e86c96a1b | c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[O-;H0;D1:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 81.1 | [{"value": 81.0, "product": "ClC1=C(C=C(C=C1)OC)NC(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.1, "product": "ClC1=C(C=C(C=C1)OC)NC(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 30 | CELSIUS | 1 | HOUR | 2-Chloro-5-methoxyaniline hydrochloride (26 g, 134 mmol) was added to acetic acid (117 ml) and water (13 ml). The slurry was warmed to 30° C. A solution of potassium cyanate (13 g, 161 mmol) in water (104 ml) was added dropwise. After 1 hour at 40° C., the reaction was cooled to 20° C., filtered and washed with water (... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Urea | null | null | c1ccccc1 | null | O | 30 | 1 | COc1ccc(Cl)c(N)c1.N#C[O-]>O>COc1ccc(Cl)c(NC(N)=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4c3711d37de04af6b2801673c3f820ea | COC(=O)C=C1CC2CCC(C1)N2C.[Li][c]1cccs1>>CN1C2CCC1CC(=CC(O)(c1cccs1)c1cccs1)C2.[NH4+].[OH-] | COC(C=C1CC2CCC(C1)N2C)=O.S1C(=CC=C1)[Li]>>[NH4+].[OH-].CN1C2CC(CC1CC2)=CC(O)(C=2SC=CC2)C=2SC=CC2 | [CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][C:8](=[CH:9][C:10](=[O:11])[O:24][CH3:12])[CH2:22]2.[Li][c:17]1[s:16][cH:15][cH:14][cH:18]1>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][C:8](=[CH:9][C:10]([OH:11])([c:12]1[cH:13][cH:14][cH:15][s:16]1)[c:17]1[cH:18][cH:19][cH:20][s:21]1)[CH2:22]2.[NH4+:23].[OH-:24] | COC(=O)C=C1CC2CCC(C1)N2C.[Li][c]1cccs1 | CN1C2CCC1CC(=CC(O)(c1cccs1)c1cccs1)C2.[NH4+].[OH-] | null | null | [NH4+].[Cl-].C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | cb5bcc5cf66f08b5117f8fd57d6c931fa0eaf03660bb28e0f4a73bc046a47144 | 01d389a1ef988a5ea0b552ba0951ad0e66e36786c8a2ad92712297c57283a47f | C(=C1CC2CCC(C1)N2)C(c1cccs1)c1cccs1 | [C:1]-[C:2](=[C:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[O;H0;D2;+0:6]-[CH3;D1;+0:7])-[C:8].[Li]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[cH;D2;+0:11]:[c:12]:[s;H0;D2;+0:13]:1>>[C:1]-[C:2](=[C:3]-[C;H0;D4;+0:4](-[OH;D1;+0:5])(-[c;H0;D3;+0:7]1:[c:14]:[cH;D2;+0:11]:[c:12]:[s;H0;D2;+0:13]:1)-[c;H0;D3;+0:9]1:[#16;a:15]:[c:16]:[c:17]:[cH;... | 78.1 | [{"value": 2.0, "product": "[NH4+].[OH-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.0, "product": "CN1C2CC(CC1CC2)=CC(O)(C=2SC=CC2)C=2SC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.1, "product": "CN1C2CC(CC1CC2)=CC(O)(C=2SC=CC2)C=2SC=CC2", "details": "CALCULATEDPERCENTYIELD"... | null | null | 8 | HOUR | A solution of (8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-acetic acid methyl ester (200 mg, 1.02 mmol) in THF (3 mL) was mixed with 2-thienyllithium (2.02 mL, 1.0 M in THF, 2.02 mmol). The mixture was stirred overnight at r.t., diluted with saturated NH4Cl aqueous solution (20 mL) and extracted with EtOAc. The combine... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aryl lithium | Tertiary alcohol | c1ccsc1 | c1ccsc1.c1ccsc1 | C1CC2CCC(C1)[NH]2.c1ccsc1.c1ccsc1 | Li | [NH4+].[Cl-].C1CCOC1 | null | 8 | COC(=O)C=C1CC2CCC(C1)N2C.[Li][c]1cccs1>[NH4+].[Cl-].C1CCOC1>CN1C2CCC1CC(=CC(O)(c1cccs1)c1cccs1)C2.[NH4+].[OH-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-514af9cf31ba4887b680bf006359b56b | COC(=O)C=C1CC2CCC(C1)N2C.[Cl][Mg][CH2]c1ccccc1>>CN1C2CCC1CC(=CC(O)(Cc1ccccc1)Cc1ccccc1)C2 | COC(C=C1CC2CCC(C1)N2C)=O.C(C1=CC=CC=C1)[Mg]Cl>>C(C1=CC=CC=C1)C(C=C1CC2CCC(C1)N2C)(CC2=CC=CC=C2)O | O([C:10]([CH:9]=[C:8]1[CH2:7][CH:6]2[N:2]([CH3:1])[CH:3]([CH2:4][CH2:5]2)[CH2:26]1)=[O:11])[CH3:19].[Cl][Mg][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][C:8](=[CH:9][C:10]([OH:11])([CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19][c:20]1[cH:21][cH:22][... | COC(=O)C=C1CC2CCC(C1)N2C.[Cl][Mg][CH2]c1ccccc1 | CN1C2CCC1CC(=CC(O)(Cc1ccccc1)Cc1ccccc1)C2 | null | null | null | C-C Coupling | OtherReaction | d9cfd08fb0ae0e08e2abfc9e2e9717581ce24fe474620e538d84c93665d152c2 | 0b91bc36d63c570fba02035c23fdcf278e8164647420394f29330caa2ac0d989 | C(=C1CC2CCC(C1)N2)C(Cc1ccccc1)Cc1ccccc1 | [C:1]-[C:2](=[C:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-O-[CH3;D1;+0:6])-[C:7].[Cl]-[Mg]-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C:1]-[C:2](=[C:3]-[C;H0;D4;+0:4](-[OH;D1;+0:5])(-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11])-[CH2;D2;+0:6]-[c:12](:[c:13]):[c:14])-[C:7] | 31 | [{"value": 31.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from (8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-acetic acid methyl ester and benzylmagnesium chloride by following the experimental procedures in Example 1 (31% yield): LCMS (ES) m/z 348 (M+H)+; 1H-NMR(CDCl3) δ 0.90 (m, 1H), 1.25 (m, 1H), 1.61 (m, 1H), 1.81 (m, 3H), 2.20 (s, 3H), 2.40 ... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ester | Tertiary alcohol | null | c1ccccc1 | C1CC2CCC(C1)[NH]2.c1ccccc1.c1ccccc1 | Mg | null | null | null | COC(=O)C=C1CC2CCC(C1)N2C.[Cl][Mg][CH2]c1ccccc1>>CN1C2CCC1CC(=CC(O)(Cc1ccccc1)Cc1ccccc1)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-98bcc45c4c96452387c7b29229477e69 | COC(=O)C=C1CC2CCC(C1)N2C.[Cl][Mg][c]1ccccc1>>CN1C2CCC1CC(=CC(O)(c1ccccc1)c1ccccc1)C2 | COC(C=C1CC2CCC(C1)N2C)=O.C1(=CC=CC=C1)[Mg]Cl>>CN1C2CC(CC1CC2)=CC(O)(C2=CC=CC=C2)C2=CC=CC=C2 | O([C:10]([CH:9]=[C:8]1[CH2:7][CH:14]2[N:2]([CH3:1])[CH:3]([CH2:4][CH2:15]2)[CH2:24]1)=[O:11])[CH3:17].[Cl][Mg][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][C:8](=[CH:9][C:10]([OH:11])([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)... | COC(=O)C=C1CC2CCC(C1)N2C.[Cl][Mg][c]1ccccc1 | CN1C2CCC1CC(=CC(O)(c1ccccc1)c1ccccc1)C2 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 109882035845b38cc5dc16781c120787dd673fe69b2cc3aa6c23500e4abea651 | 86699f3430ab47d59e6b5700fdac59e8de3d70ed63f18e2ca2dc71019642ab75 | C(=C1CC2CCC(C1)N2)C(c1ccccc1)c1ccccc1 | [C;D1;H3:1]-[N;H0;D3;+0:2]1-[C:3]2-[C:4]-[C:5](=[C:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-[CH3;D1;+0:9])-[CH2;D2;+0:10]-[CH;D3;+0:11]-1-[CH2;D2;+0:12]-[CH2;D2;+0:13]-2.[Cl]-[Mg]-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[C;D1;H3:1]-[N;H0;D3;+0:2]1-[C:3]2-[C:4]-[C:5](=[C:6]-[C;H0;D4;+0:7](-[OH;D1;+0:8])(-[c:19]3:[c:2... | 44 | [{"value": 44.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from (8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-acetic acid methyl ester and phenylmagnesium chloride by following the experimental procedures in Example 1 (44% yield): LCMS (ES) m/z 320 (M+H)+; 1H-NMR(CDCl3) δ 1.20 (m, 1H), 1.54 (m, 1H), 1.70 (m, 1H), 1.77 (m, 1H), 1.93 (m, 1H), 2.04 ... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ester.Tertiary amine | Tertiary alcohol.Tertiary amine | C1CC2CCC(C1)[NH]2.c1ccccc1 | C1CC2CCC(C1)[NH]2.c1ccccc1.c1ccccc1 | C1CC2CCC(C1)[NH]2.c1ccccc1.c1ccccc1 | Mg | null | null | null | COC(=O)C=C1CC2CCC(C1)N2C.[Cl][Mg][c]1ccccc1>>CN1C2CCC1CC(=CC(O)(c1ccccc1)c1ccccc1)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9dae07e19343494ca2fe90fa06300d88 | CI.CN1C2CCC1CC(=CC(O)(c1cccs1)c1cccs1)C2>>C[N+]1(C)C2CCC1CC(=CC(O)(c1cccs1)c1cccs1)C2.[I-] | CN1C2CC(CC1CC2)=CC(O)(C=2SC=CC2)C=2SC=CC2.CI.C(=O)([O-])[O-].[K+].[K+]>>[I-].OC(C=C1CC2CCC(C1)[N+]2(C)C)(C=2SC=CC2)C=2SC=CC2 | [CH3:1][I:24].[N:2]1([CH3:3])[CH:4]2[CH2:5][CH2:6][CH:7]1[CH2:8][C:9](=[CH:10][C:11]([OH:12])([c:13]1[cH:14][cH:15][cH:16][s:17]1)[c:18]1[cH:19][cH:20][cH:21][s:22]1)[CH2:23]2>>[CH3:1][N+:2]1([CH3:3])[CH:4]2[CH2:5][CH2:6][CH:7]1[CH2:8][C:9](=[CH:10][C:11]([OH:12])([c:13]1[cH:14][cH:15][cH:16][s:17]1)[c:18]1[cH:19][cH:2... | CI.CN1C2CCC1CC(=CC(O)(c1cccs1)c1cccs1)C2 | C[N+]1(C)C2CCC1CC(=CC(O)(c1cccs1)c1cccs1)C2.[I-] | null | null | CC#N.C(Cl)Cl | Functional Group Interconversion | OtherReaction | 16315b4d9ba4ae696eb90959c43c2d29df91c9d68f104b046ab1eda58093348c | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | C(=C1CC2CCC(C1)[NH2+]2)C(c1cccs1)c1cccs1 | [CH3;D1;+0:1]-[I;H0;D1;+0:2].[C:3]=[C:4]1-[C:5]-[C:6]2-[C:7]-[C:8]-[C:9](-[C:10]-1)-[N;H0;D3;+0:11]-2-[C;D1;H3:12]>>[C:3]=[C:4]1-[C:5]-[C:6]2-[C:7]-[C:8]-[C:9](-[C:10]-1)-[N+;H0;D4:11]-2(-[C;D1;H3:12])-[CH3;D1;+0:1].[I-;H0;D0:2] | 96 | [{"value": 96.0, "product": "[I-].OC(C=C1CC2CCC(C1)[N+]2(C)C)(C=2SC=CC2)C=2SC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.4, "product": "[I-].OC(C=C1CC2CCC(C1)[N+]2(C)C)(C=2SC=CC2)C=2SC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 2-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-1,1-di-thiophen-2-yl-ethanol (10 mg, 0.03 mmol) in CH3CN (1 mL) and CH2Cl2 (0.5 mL) was mixed with methyliodide (0.038 mL, 0.6 mmol) and K2CO3 (0.1 g, 0.7 mmol). The mixture was stirred overnight at r.t. and filtered. Separation via a reverse-phase HPLC then ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CC2CCC(C1)[NH]2 | C1CC2CCC(C1)[NH+]2 | C1CC2CCC(C1)[NH+]2.c1ccsc1.c1ccsc1 | null | CC#N.C(Cl)Cl | null | 8 | CI.CN1C2CCC1CC(=CC(O)(c1cccs1)c1cccs1)C2>CC#N.C(Cl)Cl>C[N+]1(C)C2CCC1CC(=CC(O)(c1cccs1)c1cccs1)C2.[I-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-587843cf6e104bbc853af7ec7ec04ed5 | CI.CN1C2CCC1CC(=CC(O)(Cc1ccccc1)Cc1ccccc1)C2>>C[N+]1(C)C2CCC1CC(=CC(O)(Cc1ccccc1)Cc1ccccc1)C2.[I-] | C(C1=CC=CC=C1)C(C=C1CC2CCC(C1)N2C)(CC2=CC=CC=C2)O.CI>>[I-].C(C1=CC=CC=C1)C(C=C1CC2CCC(C1)[N+]2(C)C)(CC2=CC=CC=C2)O | [CH3:1][I:28].[N:2]1([CH3:3])[CH:4]2[CH2:5][CH2:6][CH:7]1[CH2:8][C:9](=[CH:10][C:11]([OH:12])([CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[CH2:27]2>>[CH3:1][N+:2]1([CH3:3])[CH:4]2[CH2:5][CH2:6][CH:7]1[CH2:8][C:9](=[CH:10][C:11]([OH:12])([CH2:13][c:14]1[cH:15][... | CI.CN1C2CCC1CC(=CC(O)(Cc1ccccc1)Cc1ccccc1)C2 | C[N+]1(C)C2CCC1CC(=CC(O)(Cc1ccccc1)Cc1ccccc1)C2.[I-] | null | null | null | Functional Group Interconversion | OtherReaction | 16315b4d9ba4ae696eb90959c43c2d29df91c9d68f104b046ab1eda58093348c | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | C(=C1CC2CCC(C1)[NH2+]2)C(Cc1ccccc1)Cc1ccccc1 | [CH3;D1;+0:1]-[I;H0;D1;+0:2].[C:3]=[C:4]1-[C:5]-[C:6]2-[C:7]-[C:8]-[C:9](-[C:10]-1)-[N;H0;D3;+0:11]-2-[C;D1;H3:12]>>[C:3]=[C:4]1-[C:5]-[C:6]2-[C:7]-[C:8]-[C:9](-[C:10]-1)-[N+;H0;D4:11]-2(-[C;D1;H3:12])-[CH3;D1;+0:1].[I-;H0;D0:2] | 85 | [{"value": 85.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 2-benzyl-1-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-3-phenyl-propan-2-ol and methyliodide by following the experimental procedures in Example 4 (85% yield): LCMS (ES) m/z 346 (M+H)+; 1H-NMR(CDCl3) δ 0.80 (m, 1H), 1.48 (m, 1H), 1.84 (m, 1H), 1.99 (m, 1H), 2.09 (m, 2H), 2.87 (m, 1... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CC2CCC(C1)[NH]2 | C1CC2CCC(C1)[NH+]2 | C1CC2CCC(C1)[NH+]2.c1ccccc1.c1ccccc1 | null | null | null | null | CI.CN1C2CCC1CC(=CC(O)(Cc1ccccc1)Cc1ccccc1)C2>>C[N+]1(C)C2CCC1CC(=CC(O)(Cc1ccccc1)Cc1ccccc1)C2.[I-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2c9484adda5b465bba157e391c1695b8 | CI.CN1C2CCC1CC(=CC(O)(c1ccccc1)c1ccccc1)C2>>C[N+]1(C)C2CCC1CC(=CC(O)(c1ccccc1)c1ccccc1)C2.[I-] | CN1C2CC(CC1CC2)=CC(O)(C2=CC=CC=C2)C2=CC=CC=C2.CI>>[I-].OC(C=C1CC2CCC(C1)[N+]2(C)C)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH3:1][I:26].[N:2]1([CH3:3])[CH:4]2[CH2:5][CH2:6][CH:7]1[CH2:8][C:9](=[CH:10][C:11]([OH:12])([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[CH2:25]2>>[CH3:1][N+:2]1([CH3:3])[CH:4]2[CH2:5][CH2:6][CH:7]1[CH2:8][C:9](=[CH:10][C:11]([OH:12])([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:... | CI.CN1C2CCC1CC(=CC(O)(c1ccccc1)c1ccccc1)C2 | C[N+]1(C)C2CCC1CC(=CC(O)(c1ccccc1)c1ccccc1)C2.[I-] | null | null | null | Functional Group Interconversion | OtherReaction | 16315b4d9ba4ae696eb90959c43c2d29df91c9d68f104b046ab1eda58093348c | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | C(=C1CC2CCC(C1)[NH2+]2)C(c1ccccc1)c1ccccc1 | [CH3;D1;+0:1]-[I;H0;D1;+0:2].[C:3]=[C:4]1-[C:5]-[C:6]2-[C:7]-[C:8]-[C:9](-[C:10]-1)-[N;H0;D3;+0:11]-2-[C;D1;H3:12]>>[C:3]=[C:4]1-[C:5]-[C:6]2-[C:7]-[C:8]-[C:9](-[C:10]-1)-[N+;H0;D4:11]-2(-[C;D1;H3:12])-[CH3;D1;+0:1].[I-;H0;D0:2] | 67 | [{"value": 67.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 2-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-1,1-diphenyl-ethanol and methyliodide by following the experimental procedures in Example 4 (67% yield): LCMS (ES) m/z 334 (M+H)+; 1H-NMR(CDCl3) δ 1.50 (m, 1H), 1.98 (m, 1H), 2.11 (m, 1H), 2.35 (m, 2H), 2.87 (m, 1H), 2.96 (m, 1H), 3.23 ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CC2CCC(C1)[NH]2 | C1CC2CCC(C1)[NH+]2 | C1CC2CCC(C1)[NH+]2.c1ccccc1.c1ccccc1 | null | null | null | null | CI.CN1C2CCC1CC(=CC(O)(c1ccccc1)c1ccccc1)C2>>C[N+]1(C)C2CCC1CC(=CC(O)(c1ccccc1)c1ccccc1)C2.[I-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7891fb96a57840c0b1b30def96b4804c | C[C@H](N)C(F)(F)F.Fc1cc(F)c(-c2c(Cl)nc3ncnn3c2Cl)c(F)c1>>C[C@H](Nc1c(-c2c(F)cc(F)cc2F)c(Cl)nc2ncnn12)C(F)(F)F | ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)F)F)Cl)N=CN2.Cl.FC([C@H](C)N)(F)F.C(C)(C)N(C(C)C)CC>>ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)F)F)N[C@H](C(F)(F)F)C)N=CN2 | [CH3:1][C@H:2]([NH2:3])[C:23]([F:24])([F:25])[F:26].Cl[c:4]1[c:5](-[c:6]2[c:7]([F:8])[cH:9][c:10]([F:11])[cH:12][c:13]2[F:14])[c:15]([Cl:16])[n:17][c:18]2[n:19][cH:20][n:21][n:22]12>>[CH3:1][C@H:2]([NH:3][c:4]1[c:5](-[c:6]2[c:7]([F:8])[cH:9][c:10]([F:11])[cH:12][c:13]2[F:14])[c:15]([Cl:16])[n:17][c:18]2[n:19][cH:20][n:... | C[C@H](N)C(F)(F)F.Fc1cc(F)c(-c2c(Cl)nc3ncnn3c2Cl)c(F)c1 | C[C@H](Nc1c(-c2c(F)cc(F)cc2F)c(Cl)nc2ncnn12)C(F)(F)F | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 680ce65987443e27ed1de90a7e61da2b858a904becdcfebe764b8f0fdb130b5c | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cnc3ncnn3c2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]2:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:2:[#7;a:7]:[c:8](-[Cl;D1;H0:9]):[c:10]:1-[c:11].[C;D1;H3:12]-[C:13](-[NH2;D1;+0:14])-[C:15](-[F;D1;H0:16])(-[F;D1;H0:17])-[F;D1;H0:18]>>[C;D1;H3:12]-[C:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[#7;a:2]2:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:2:[#7;a:7]:[c:8](-[Cl;D1;H0:9]):[c... | 95.7 | [{"value": 95.7, "product": "ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)F)F)N[C@H](C(F)(F)F)C)N=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 13 | HOUR | A mixture of 5,7-dichloro-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine (3.0 g, 9.4 mmol), (1S)-2,2,2-trifluoro-1-methylethylamine hydrogen chloride (4.2 g, 28.2 mmol), and N,N-diisopropylethylamine (4.9 mL, 28.2 mmol) in 100 mL of N,N-dimethylformamide is stirred at room temperature under nitrogen atmosphe... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2ncnn2c1 | c1cnc2ncnn2c1 | c1ccccc1.c1cnc2ncnn2c1 | HCl | CN(C=O)C.C(C)(=O)OCC | null | 13 | C[C@H](N)C(F)(F)F.Fc1cc(F)c(-c2c(Cl)nc3ncnn3c2Cl)c(F)c1>CN(C=O)C.C(C)(=O)OCC>C[C@H](Nc1c(-c2c(F)cc(F)cc2F)c(Cl)nc2ncnn12)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-421dbdeda10342f28090350c0dc828e7 | CN(C)CCCO.C[C@H](Nc1c(-c2c(F)cc(F)cc2F)c(Cl)nc2ncnn12)C(F)(F)F>>C[C@H](Nc1c(-c2c(F)cc(OCCCN(C)C)cc2F)c(Cl)nc2ncnn12)C(F)(F)F | O.ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)F)F)N[C@H](C(F)(F)F)C)N=CN2.CN(CCCO)C.[H-].[Na+]>>ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)OCCCN(C)C)F)N[C@H](C(F)(F)F)C)N=CN2 | [OH:11][CH2:12][CH2:13][CH2:14][N:15]([CH3:16])[CH3:17].F[c:10]1[cH:9][c:7]([F:8])[c:6](-[c:5]2[c:4]([NH:3][C@@H:2]([CH3:1])[C:29]([F:30])([F:31])[F:32])[n:28]3[c:24]([n:23][c:21]2[Cl:22])[n:25][cH:26][n:27]3)[c:19]([F:20])[cH:18]1>>[CH3:1][C@H:2]([NH:3][c:4]1[c:5](-[c:6]2[c:7]([F:8])[cH:9][c:10]([O:11][CH2:12][CH2:13]... | CN(C)CCCO.C[C@H](Nc1c(-c2c(F)cc(F)cc2F)c(Cl)nc2ncnn12)C(F)(F)F | C[C@H](Nc1c(-c2c(F)cc(OCCCN(C)C)cc2F)c(Cl)nc2ncnn12)C(F)(F)F | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(-c2cnc3ncnn3c2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 67.7 | [{"value": 67.7, "product": "ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)OCCCN(C)C)F)N[C@H](C(F)(F)F)C)N=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a solution of 5-chloro-6-(2,4,6-trifluorophenyl)-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine (600 mg, 1.5 mmol) and 3-dimethylamino-1-propanol (1.03 g, 10 mmol) in 5 mL of dimethylsulfoxide at room temperature is added sodium hydride (60% in mineral oil, 400 mg, 10 mmol). The mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cnc2ncnn2c1 | HF | CS(=O)C | 50 | null | CN(C)CCCO.C[C@H](Nc1c(-c2c(F)cc(F)cc2F)c(Cl)nc2ncnn12)C(F)(F)F>CS(=O)C>C[C@H](Nc1c(-c2c(F)cc(OCCCN(C)C)cc2F)c(Cl)nc2ncnn12)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15120b4bcb65405e8de97b2df43db45d | CNCCCO.C[C@H](Nc1c(-c2c(F)cc(F)cc2F)c(Cl)nc2ncnn12)C(F)(F)F>>CNCCCOc1cc(F)c(-c2c(Cl)nc3ncnn3c2N[C@@H](C)C(F)(F)F)c(F)c1 | [H-].[Na+].CNCCCO.ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)F)F)N[C@H](C(F)(F)F)C)N=CN2>>ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)OCCCNC)F)N[C@H](C(F)(F)F)C)N=CN2 | [CH3:1][NH:2][CH2:3][CH2:4][CH2:5][OH:6].F[c:7]1[cH:8][c:9]([F:10])[c:11](-[c:12]2[c:13]([Cl:14])[n:15][c:16]3[n:17][cH:18][n:19][n:20]3[c:21]2[NH:22][C@@H:23]([CH3:24])[C:25]([F:26])([F:27])[F:28])[c:29]([F:30])[cH:31]1>>[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][c:9]([F:10])[c:11](-[c:12]2[c:13]([Cl:14])[n:1... | CNCCCO.C[C@H](Nc1c(-c2c(F)cc(F)cc2F)c(Cl)nc2ncnn12)C(F)(F)F | CNCCCOc1cc(F)c(-c2c(Cl)nc3ncnn3c2N[C@@H](C)C(F)(F)F)c(F)c1 | null | null | CS(=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(-c2cnc3ncnn3c2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 40.3 | [{"value": 40.3, "product": "ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)OCCCNC)F)N[C@H](C(F)(F)F)C)N=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To sodium hydride (60% in mineral oil, 2.3 g, 57.6 mmol) in 20 mL of dimethylsulfoxide at room temperature is added a solution of 3-(methylamino)propan-1-ol (5.14 g, 57.6 mmol) in 10 mL of dimethylsulfoxide. The solution is stirred at room temperature for 1 h, and 5-chloro-6-(2,4,6-trifluorophenyl)-N-[(1S)-2,2,2-triflu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cnc2ncnn2c1 | HF | CS(=O)C.C(C)(=O)OCC | null | 1 | CNCCCO.C[C@H](Nc1c(-c2c(F)cc(F)cc2F)c(Cl)nc2ncnn12)C(F)(F)F>CS(=O)C.C(C)(=O)OCC>CNCCCOc1cc(F)c(-c2c(Cl)nc3ncnn3c2N[C@@H](C)C(F)(F)F)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b9c8180031aa41cca7822ea0b32bd159 | O=C(O)/C=C/C(=O)O>>O=C(O)/C=C/C(=O)O | C(\C=C\C(=O)O)(=O)O.Cl.ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)OCCCNC)F)N[C@H](C(F)(F)F)C)N=CN2.[OH-].[Na+]>>C(\C=C\C(=O)O)(=O)O.ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)OCCCNC)F)N[C@H](C(F)(F)F)C)N=CN2 | [O:32]=[C:33]([OH:34])/[CH:35]=[CH:36]/[C:37](=[O:38])[OH:39]>>[O:32]=[C:33]([OH:34])/[CH:35]=[CH:36]/[C:37](=[O:38])[OH:39] | O=C(O)/C=C/C(=O)O | O=C(O)/C=C/C(=O)O | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 75.1 | [{"value": 75.0, "product": "C(\\C=C\\C(=O)O)(=O)O.ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)OCCCNC)F)N[C@H](C(F)(F)F)C)N=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.1, "product": "C(\\C=C\\C(=O)O)(=O)O.ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)OCCCNC)F)N[C@H](C(F)(F)F)C)N=CN2", "details": "CALCULATEDPERCENTYIELD", "... | 70 | CELSIUS | 17.5 | MINUTE | To a slurry of 5-chloro-6-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine hydrochloride (7.50 g, 15.0 mmol) and water (100 mL) is added sodium hydroxide solution (10 N, 2.0 mL, 20 mmol) dropwise. Then, fumaric acid (3.48 g, 30 mmol) is added.... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | 70 | 0.291667 | O=C(O)/C=C/C(=O)O>O>O=C(O)/C=C/C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-999b25e3cb2d4cecb12b24dfd9489389 | O=C(O)CCC(=O)O>>O=C(O)CCC(=O)O | ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)OCCCNC)F)N[C@H](C(F)(F)F)C)N=CN2.C(CCC(=O)O)(=O)O>>C(CCC(=O)O)(=O)O.ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)OCCCNC)F)N[C@H](C(F)(F)F)C)N=CN2 | [O:32]=[C:33]([OH:34])[CH2:35][CH2:36][C:37](=[O:38])[OH:39]>>[O:32]=[C:33]([OH:34])[CH2:35][CH2:36][C:37](=[O:38])[OH:39] | O=C(O)CCC(=O)O | O=C(O)CCC(=O)O | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 70 | CELSIUS | 17.5 | MINUTE | A mixture of 5-chloro-6-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine (9.00 g, 19.4 mmol) and succinic acid (2.75 g, 23.3 mmol) in water (90 mL) is stirred for about 15-20 min and then heated to about 65-75° C. The solution is filtered and ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | 70 | 0.291667 | O=C(O)CCC(=O)O>O>O=C(O)CCC(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c47997c64243437f9f2f3d828ae764c4 | C[C@H](N)C(F)(F)F.Fc1cc(F)c(-c2c(Br)nc3ncnn3c2Br)c(F)c1>>C[C@H](Nc1c(-c2c(F)cc(F)cc2F)c(Br)nc2ncnn12)C(F)(F)F | O.BrC1=NC=2N(C(=C1C1=C(C=C(C=C1F)F)F)Br)N=CN2.Cl.FC([C@H](C)N)(F)F.C(C)(C)N(CC)C(C)C>>BrC1=NC=2N(C(=C1C1=C(C=C(C=C1F)F)F)N[C@H](C(F)(F)F)C)N=CN2 | [CH3:1][C@H:2]([NH2:3])[C:23]([F:24])([F:25])[F:26].Br[c:4]1[c:5](-[c:6]2[c:7]([F:8])[cH:9][c:10]([F:11])[cH:12][c:13]2[F:14])[c:15]([Br:16])[n:17][c:18]2[n:19][cH:20][n:21][n:22]12>>[CH3:1][C@H:2]([NH:3][c:4]1[c:5](-[c:6]2[c:7]([F:8])[cH:9][c:10]([F:11])[cH:12][c:13]2[F:14])[c:15]([Br:16])[n:17][c:18]2[n:19][cH:20][n:... | C[C@H](N)C(F)(F)F.Fc1cc(F)c(-c2c(Br)nc3ncnn3c2Br)c(F)c1 | C[C@H](Nc1c(-c2c(F)cc(F)cc2F)c(Br)nc2ncnn12)C(F)(F)F | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 680ce65987443e27ed1de90a7e61da2b858a904becdcfebe764b8f0fdb130b5c | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cnc3ncnn3c2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]2:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:2:[#7;a:7]:[c:8](-[Br;D1;H0:9]):[c:10]:1-[c:11].[C;D1;H3:12]-[C:13](-[NH2;D1;+0:14])-[C:15](-[F;D1;H0:16])(-[F;D1;H0:17])-[F;D1;H0:18]>>[Br;D1;H0:9]-[c:8]1:[#7;a:7]:[c:6]2:[#7;a:5]:[c:4]:[#7;a:3]:[#7;a:2]:2:[c;H0;D3;+0:1](-[NH;D2;+0:14]-[C:13](-[C;D1;H3:12])-[C... | 17.5 | [{"value": 17.5, "product": "BrC1=NC=2N(C(=C1C1=C(C=C(C=C1F)F)F)N[C@H](C(F)(F)F)C)N=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of 5,7-dibromo-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine (320 mg, 0.78 mmol), (1S)-2,2,2-trifluoro-1-methylethylamine hydrogen chloride (235 mg, 1.57 mmol), and diisopropylethylamine (260 mg, 2.0 mmol) in 5 mL of N,N-dimethylformamide is stirred at room temperature for 18 h. Water is added to ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2ncnn2c1 | c1cnc2ncnn2c1 | c1ccccc1.c1cnc2ncnn2c1 | HBr | CN(C=O)C | null | 18 | C[C@H](N)C(F)(F)F.Fc1cc(F)c(-c2c(Br)nc3ncnn3c2Br)c(F)c1>CN(C=O)C>C[C@H](Nc1c(-c2c(F)cc(F)cc2F)c(Br)nc2ncnn12)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-598882ca8c114ffba921317d4c245de0 | CN(C)CCCO.C[C@H](Nc1c(-c2c(F)cc(F)cc2F)c(Br)nc2ncnn12)C(F)(F)F>>C[C@H](Nc1c(-c2c(F)cc(OCCCN(C)C)cc2F)c(Br)nc2ncnn12)C(F)(F)F | O.BrC1=NC=2N(C(=C1C1=C(C=C(C=C1F)F)F)N[C@H](C(F)(F)F)C)N=CN2.CN(CCCO)C.[H-].[Na+]>>BrC1=NC=2N(C(=C1C1=C(C=C(C=C1F)OCCCN(C)C)F)N[C@H](C(F)(F)F)C)N=CN2 | [OH:11][CH2:12][CH2:13][CH2:14][N:15]([CH3:16])[CH3:17].F[c:10]1[cH:9][c:7]([F:8])[c:6](-[c:5]2[c:4]([NH:3][C@@H:2]([CH3:1])[C:29]([F:30])([F:31])[F:32])[n:28]3[c:24]([n:23][c:21]2[Br:22])[n:25][cH:26][n:27]3)[c:19]([F:20])[cH:18]1>>[CH3:1][C@H:2]([NH:3][c:4]1[c:5](-[c:6]2[c:7]([F:8])[cH:9][c:10]([O:11][CH2:12][CH2:13]... | CN(C)CCCO.C[C@H](Nc1c(-c2c(F)cc(F)cc2F)c(Br)nc2ncnn12)C(F)(F)F | C[C@H](Nc1c(-c2c(F)cc(OCCCN(C)C)cc2F)c(Br)nc2ncnn12)C(F)(F)F | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(-c2cnc3ncnn3c2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 78.3 | [{"value": 78.3, "product": "BrC1=NC=2N(C(=C1C1=C(C=C(C=C1F)OCCCN(C)C)F)N[C@H](C(F)(F)F)C)N=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a solution of 5-bromo-6-(2,4,6-trifluorophenyl)-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine (44 mg, 0.1 mmol) and 3-dimethylamino-1-propanol (51 m g, 0.5 mmol) in 1 mL of dimethylsulfoxide at room temperature is added sodium hydride (60% in mineral oil, 20 mg, 0.5 mmol). The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cnc2ncnn2c1 | HF | CS(=O)C | 60 | null | CN(C)CCCO.C[C@H](Nc1c(-c2c(F)cc(F)cc2F)c(Br)nc2ncnn12)C(F)(F)F>CS(=O)C>C[C@H](Nc1c(-c2c(F)cc(OCCCN(C)C)cc2F)c(Br)nc2ncnn12)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-46c8f9dfedd640ea8424108be2403a20 | CCOC(=O)C(C(=O)OCC)c1c(F)cc(OC)cc1F>>CCOC(=O)C(C(=O)OCC)c1c(F)cc(O)cc1F | C([O-])(O)=O.[Na+].FC1=C(C(=CC(=C1)OC)F)C(C(=O)OCC)C(=O)OCC.B(Br)(Br)Br>>FC1=C(C(=CC(=C1)O)F)C(C(=O)OCC)C(=O)OCC | C[O:17][c:16]1[cH:15][c:13]([F:14])[c:12]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[O:9][CH2:10][CH3:11])[c:19]([F:20])[cH:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[c:12]1[c:13]([F:14])[cH:15][c:16]([OH:17])[cH:18][c:19]1[F:20] | CCOC(=O)C(C(=O)OCC)c1c(F)cc(OC)cc1F | CCOC(=O)C(C(=O)OCC)c1c(F)cc(O)cc1F | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 94.7 | [{"value": 94.7, "product": "FC1=C(C(=CC(=C1)O)F)C(C(=O)OCC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 10 | MINUTE | To a solution of diethyl 2-(2,6-difluoro-4-methoxyphenyl)malonate (2.11 g, 7.0 mmol) in 60 mL of methylene chloride at −78° C. is added boron tribromide (2.65 mL, 28 mmol) dropwise. The mixture is then stirred at −78° C. for 10 minutes, warmed to 0° C., and stirred at 0° C. for 1 h. A 5% aqueous solution of sodium bica... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | C(Cl)Cl | -78 | 0.166667 | CCOC(=O)C(C(=O)OCC)c1c(F)cc(OC)cc1F>C(Cl)Cl>CCOC(=O)C(C(=O)OCC)c1c(F)cc(O)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d939f4404c241e5b2b77e09326f51eb | C=CCCO.CCOC(=O)C(C(=O)OCC)c1c(F)cc(OS(=O)(=O)C(F)(F)F)cc1F>>CCOC(=O)C(C(=O)OCC)c1c(F)cc(CCCCO)cc1F | C[N+](C)(C)[O-].FC1=C(C(=CC(=C1)OS(=O)(=O)C(F)(F)F)F)C(C(=O)OCC)C(=O)OCC.P(=O)([O-])([O-])[O-].[K+].[K+].[K+].C12CCCC(CCC1)B2.O1CCCC1.C(CC=C)O>>FC1=C(C(=CC(=C1)CCCCO)F)C(C(=O)OCC)C(=O)OCC | [CH2:17]=[CH:18][CH2:19][CH2:20][OH:21].O=S(=O)(O[c:16]1[cH:15][c:13]([F:14])[c:12]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[O:9][CH2:10][CH3:11])[c:23]([F:24])[cH:22]1)C(F)(F)F>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[c:12]1[c:13]([F:14])[cH:15][c:16]([CH2:17][CH2:18][CH... | C=CCCO.CCOC(=O)C(C(=O)OCC)c1c(F)cc(OS(=O)(=O)C(F)(F)F)cc1F | CCOC(=O)C(C(=O)OCC)c1c(F)cc(CCCCO)cc1F | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1.C(C)(=O)OCC | C-C Coupling | OtherReaction | 984b78f4f8d59098e10d908843a5bc85917f55238c2f2137d4efc412864d5e7c | dc8d671a2733f8ed24a0522b611e130eb3e91983213ee2751322bb6d51e1830f | c1ccccc1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[CH;D2;+0:8]=[CH2;D1;+0:9]>>[C:6]-[C:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 42.7 | [{"value": 42.7, "product": "FC1=C(C(=CC(=C1)CCCCO)F)C(C(=O)OCC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a 0.5 M solution of 9-borabicyclo[3.3.1]nonane (9-BBN) in tetrahydrofuran (95 mL, 47.6 mmol) is added dropwise 3-butene-1-ol (4.1 mL, 47.6 mmol), and the mixture is stirred under nitrogen atmosphere at room temperature for 6 h. The resulting solution is then transferred by a double-ended needle into a mixture of die... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Allyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | TfOH | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(C)(=O)OCC | null | 6 | C=CCCO.CCOC(=O)C(C(=O)OCC)c1c(F)cc(OS(=O)(=O)C(F)(F)F)cc1F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(C)(=O)OCC>CCOC(=O)C(C(=O)OCC)c1c(F)cc(CCCCO)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d092c670c40a423091b1f4ce5020007d | CCN(CC)CC.CCNCC.O=C([O-])C(C(=O)[O-])c1c(F)cc(CCCCO)cc1F>>CCOC(=O)C(C(=O)OCC)c1c(F)cc(CCCCN(C)C)cc1F | C(C)NCC.O1CCCC1.FC1=C(C(=CC(=C1)CCCCO)F)C(C(=O)[O-])C(=O)[O-].C(C)N(CC)CC.CS(=O)(=O)Cl>>CN(CCCCC1=CC(=C(C(=C1)F)C(C(=O)OCC)C(=O)OCC)F)C | CCN(CC)[CH2:2][CH3:1].[CH2:10]([CH3:11])[NH:21][CH2:22][CH3:23].O[CH2:20][CH2:19][CH2:18][CH2:17][c:16]1[cH:15][c:13]([F:14])[c:12]([CH:6]([C:4]([O-:3])=[O:5])[C:7](=[O:8])[O-:9])[c:25]([F:26])[cH:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[c:12]1[c:13]([F:14])[cH:15][c:16]([CH2:17]... | CCN(CC)CC.CCNCC.O=C([O-])C(C(=O)[O-])c1c(F)cc(CCCCO)cc1F | CCOC(=O)C(C(=O)OCC)c1c(F)cc(CCCCN(C)C)cc1F | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | ea1d3c1d4a39334b9eb50b36f005cb6aa33430995fc3f0d75d155838aa416985 | f35b1eede046205811cbd9c28631f641d27eb5341a50b573f6e75427ea64ca20 | c1ccccc1 | C-C-N(-C-C)-[CH2;D2;+0:1]-[C;D1;H3:2].O-[CH2;D2;+0:3]-[C:4]-[C:5].[O-;H0;D1:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10](-[O-;H0;D1:11])=[O;D1;H0:12].[C;D1;H3:13]-[CH2;D2;+0:14]-[NH;D2;+0:15]-[CH2;D2;+0:16]-[CH3;D1;+0:17]>>[C;D1;H3:13]-[CH2;D2;+0:14]-[O;H0;D2;+0:11]-[C:10](=[O;D1;H0:12])-[C:9]-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:6]... | null | [] | null | null | null | null | To a solution of 2-[2,6-difluoro-4-(4-hydroxybutyl)phenyl]malonate (2.0 g, 5.8 mmol) and triethylamine (2.43 mL, 17.4 mmol) in 15 ml of methylene chloride at 0° C. is added methanesulfonyl chloride (0.898 mL, 11.6 mmol). The resulting mixture is allowed to warm to room temperature in 1.5 h. The mixture is washed with 1... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine.Tertiary amine | Ester.Ester.Tertiary amine | null | null | c1ccccc1 | HO- | C(Cl)Cl | null | null | CCN(CC)CC.CCNCC.O=C([O-])C(C(=O)[O-])c1c(F)cc(CCCCO)cc1F>C(Cl)Cl>CCOC(=O)C(C(=O)OCC)c1c(F)cc(CCCCN(C)C)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a61d1b6715b43a299f9e27b945d04ce | CCOC(=O)C(C(=O)OCC)c1c(F)cc(CCCCN(C)C)cc1F.Nc1nc[nH]n1>>CN(C)CCCCc1cc(F)c(-c2c(O)nc3ncnn3c2O)c(F)c1 | CN(CCCCC1=CC(=C(C(=C1)F)C(C(=O)OCC)C(=O)OCC)F)C.NC1=NNC=N1.C(CCC)N(CCCC)CCCC>>CN(CCCCC1=CC(=C(C(=C1)F)C=1C(=NC=2N(C1O)N=CN2)O)F)C | CCO[C:14]([CH:13]([c:12]1[c:10]([F:11])[cH:9][c:8]([CH2:7][CH2:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[cH:26][c:24]1[F:25])[C:22](OCC)=[O:23])=[O:15].[NH2:16][c:17]1[n:18][cH:19][nH:20][n:21]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][c:8]1[cH:9][c:10]([F:11])[c:12](-[c:13]2[c:14]([OH:15])[n:16][c:17]3[n:18][cH... | CCOC(=O)C(C(=O)OCC)c1c(F)cc(CCCCN(C)C)cc1F.Nc1nc[nH]n1 | CN(C)CCCCc1cc(F)c(-c2c(O)nc3ncnn3c2O)c(F)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ac7d5d1285ecbc0fc0c7df5cb8115ebe0ad026b9f23bb1406929cb0426c46965 | 6504f33921726f64e36c5f3f322459b73652319c83071522ec21b8b88a33a5a7 | c1ccc(-c2cnc3ncnn3c2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-O-C-C)-[c;H0;D3;+0:6](:[c:7](-[F;D1;H0:8]):[c:9]):[c:10](-[F;D1;H0:11]):[c:12].[NH2;D1;+0:13]-[c:14]1:[#7;a:15]:[c:16]:[nH;D2;+0:17]:[n;H0;D2;+0:18]:1>>[F;D1;H0:8]-[c:7](:[c:9]):[c;H0;D3;+0:6](-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[OH;D1;+0:... | 81 | [{"value": 81.0, "product": "CN(CCCCC1=CC(=C(C(=C1)F)C=1C(=NC=2N(C1O)N=CN2)O)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | 16 | HOUR | A mixture of diethyl 2-{4-[4-(dimethylamino)butyl]-2,6-difluorophenyl]malonate (1.0 g, 2.7 mmol), 3-amino-1,2,4-triazole (250 mg, 3.0 mmol), and tributylamine (0.71 mL, 3.0 mmol) is stirred under nitrogen atmosphere at 160° C. for 16 h and cooled to room temperature. The mixture is stirred with 20 ml of hexanes. The pr... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Aromatic alcohol.Aromatic alcohol | c1nnc[nH]1 | c1cnc2ncnn2c1 | c1ccccc1.c1cnc2ncnn2c1 | HO- | null | 160 | 16 | CCOC(=O)C(C(=O)OCC)c1c(F)cc(CCCCN(C)C)cc1F.Nc1nc[nH]n1>>CN(C)CCCCc1cc(F)c(-c2c(O)nc3ncnn3c2O)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-013a65e7184744e295e31a6ef981ae6d | CCI.O=C(O)Cc1c(F)cc(F)cc1F>>CCOC(=O)Cc1c(F)cc(F)cc1F | FC1=C(C(=CC(=C1)F)F)CC(=O)O.ICC.C([O-])([O-])=O.[K+].[K+]>>FC1=C(C(=CC(=C1)F)F)CC(=O)OCC | I[CH2:2][CH3:1].[OH:3][C:4](=[O:5])[CH2:6][c:7]1[c:8]([F:9])[cH:10][c:11]([F:12])[cH:13][c:14]1[F:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[c:8]([F:9])[cH:10][c:11]([F:12])[cH:13][c:14]1[F:15] | CCI.O=C(O)Cc1c(F)cc(F)cc1F | CCOC(=O)Cc1c(F)cc(F)cc1F | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccccc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C;D1;H3:2] | 88.7 | [{"value": 88.7, "product": "FC1=C(C(=CC(=C1)F)F)CC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 3 | HOUR | A mixture of 2,4,6-trifluorophenylacetic acid (570 mg, 3.0 mmol), iodoethane (1.56 g, 10 mmol), and potassium carbonate (1.38 g, 10 mmol) in 5 mL of dimethylsulfoxide is stirred at 50° C. for 3 h, and cooled to room temperature. The mixture is partitioned between diethyl ether and water. The organic layer is washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1 | HI | CS(=O)C | 50 | 3 | CCI.O=C(O)Cc1c(F)cc(F)cc1F>CS(=O)C>CCOC(=O)Cc1c(F)cc(F)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-782ec82f14a14050bce378ccea8104f8 | CCOC(=O)Cc1c(F)cc(F)cc1F.O=C(Cl)C1CCCCCC1>>CCOC(=O)C(C(=O)C1CCCCCC1)c1c(F)cc(F)cc1F | Cl.C(C)(C)[N-]C(C)C.[Li+].FC1=C(C(=CC(=C1)F)F)CC(=O)OCC.C1(CCCCCC1)C(=O)Cl>>C1(CCCCCC1)C(C(C(=O)OCC)C1=C(C=C(C=C1F)F)F)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:16]1[c:17]([F:18])[cH:19][c:20]([F:21])[cH:22][c:23]1[F:24].Cl[C:7](=[O:8])[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[c:16]1[c:17]([F:18])[cH:19][c:20]([... | CCOC(=O)Cc1c(F)cc(F)cc1F.O=C(Cl)C1CCCCCC1 | CCOC(=O)C(C(=O)C1CCCCCC1)c1c(F)cc(F)cc1F | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 9c255438d8e6adeba9ee52582b8e97af5f85bef382cd416953270ac55bd10486 | 4c7bc8856483317e0c04a17d8cd6aba13cdf5ed9f64b61fe01f230a819039f82 | O=C(Cc1ccccc1)C1CCCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:10](-[C:8](=[O;D1;H0:9])-[#8:7]-[C:6])-[c:11](:[c:12]):[c:13])-[C:5] | 59.9 | [{"value": 59.9, "product": "C1(CCCCCC1)C(C(C(=O)OCC)C1=C(C=C(C=C1F)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of ethyl 2,4,6-trifluorophenylacetate (436 mg, 2.0 mmol) in 3 mL of tetrahydrofuran is cooled to −78° C., and lithium diisopropylamide (2.0 M in heptane/tetrahydrofuran/ethylbenzene, 1.0 mL, 2.0 mmol) is added dropwise with stirring. The mixture is stirred at −78° C. for 1 h, and cycloheptanecarboxylic acid ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester | Ketone | null | null | C1CCCCCC1.c1ccccc1 | HCl | O1CCCC1 | null | null | CCOC(=O)Cc1c(F)cc(F)cc1F.O=C(Cl)C1CCCCCC1>O1CCCC1>CCOC(=O)C(C(=O)C1CCCCCC1)c1c(F)cc(F)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5bec2205b16f45e0a6de23685051a431 | CCOC(=O)C(C(=O)C1CCCCCC1)c1c(F)cc(F)cc1F.Nc1nc[nH]n1>>Oc1nc2ncnn2c(C2CCCCCC2)c1-c1c(F)cc(F)cc1F | C1(CCCCCC1)C(C(C(=O)OCC)C1=C(C=C(C=C1F)F)F)=O.NC1=NNC=N1.C(CCC)N(CCCC)CCCC>>C1(CCCCCC1)C1=C(C(=NC=2N1N=CN2)O)C2=C(C=C(C=C2F)F)F | CCO[C:2](=[O:1])[CH:17]([C:9](=O)[CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[c:18]1[c:19]([F:20])[cH:21][c:22]([F:23])[cH:24][c:25]1[F:26].[NH2:3][c:4]1[n:5][cH:6][nH:7][n:8]1>>[OH:1][c:2]1[n:3][c:4]2[n:5][cH:6][n:7][n:8]2[c:9]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[c:17]1-[c:18]1[c:1... | CCOC(=O)C(C(=O)C1CCCCCC1)c1c(F)cc(F)cc1F.Nc1nc[nH]n1 | Oc1nc2ncnn2c(C2CCCCCC2)c1-c1c(F)cc(F)cc1F | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 7674ff7d462a618e5b3752017402cc7a7f8449f1e25dd52bd8b91ea1a45dc06e | e4cbab44abd9117eb42f959793b157d31b1dce9de3f9c3954c67bf975e572e43 | c1ccc(-c2cnc3ncnn3c2C2CCCCCC2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[C;H0;D3;+0:4](=O)-[C:5](-[C:6])-[C:7])-[c;H0;D3;+0:8](:[c:9](-[F;D1;H0:10]):[c:11]):[c:12](-[F;D1;H0:13]):[c:14].[NH2;D1;+0:15]-[c:16]1:[#7;a:17]:[c:18]:[nH;D2;+0:19]:[n;H0;D2;+0:20]:1>>[C:6]-[C:5](-[c;H0;D3;+0:4]1:[c;H0;D3;+0:3](-[c;H0;D3;+0:8](:[c:9](-[F;D1;H0:10])... | 62.1 | [{"value": 62.1, "product": "C1(CCCCCC1)C1=C(C(=NC=2N1N=CN2)O)C2=C(C=C(C=C2F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | 2.5 | HOUR | A mixture of ethyl 3-cycloheptyl-3-oxo-2-(2,4,6-trifluorophenyl)propanoate (342 mg, 1.0 mmol), 3-amino-1,2,4-triazole (84 mg, 1.0 mmol), and tributylamine (185 mg, 1.0 mmol) is stirred under nitrogen atmosphere at 160° C. for 2.5 h and cooled to room temperature. The mixture is dissolved in ethyl acetate and the organi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Aromatic alcohol | c1nnc[nH]1 | c1cnc2ncnn2c1 | c1cnc2ncnn2c1.C1CCCCCC1.c1ccccc1 | HO- | C(C)(=O)OCC | 160 | 2.5 | CCOC(=O)C(C(=O)C1CCCCCC1)c1c(F)cc(F)cc1F.Nc1nc[nH]n1>C(C)(=O)OCC>Oc1nc2ncnn2c(C2CCCCCC2)c1-c1c(F)cc(F)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-12ea2415dfc34ab38ffedece9c45e59f | COc1ccc(COCCCO)cc1.Oc1nc2ncnn2c(C2CCCCCC2)c1-c1c(F)cc(F)cc1F>>COc1ccc(COCCCOc2cc(F)c(-c3c(O)nc4ncnn4c3C3CCCCCC3)c(F)c2)cc1 | C1(CCCCCC1)C1=C(C(=NC=2N1N=CN2)O)C2=C(C=C(C=C2F)F)F.COC1=CC=C(COCCCO)C=C1.[H-].[Na+]>>C1(CCCCCC1)C1=C(C(=NC=2N1N=CN2)O)C2=C(C=C(C=C2F)OCCCOCC2=CC=C(C=C2)OC)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][CH2:9][CH2:10][CH2:11][OH:12])[cH:38][cH:39]1.F[c:13]1[cH:14][c:15]([F:16])[c:17](-[c:18]2[c:19]([OH:20])[n:21][c:22]3[n:23][cH:24][n:25][n:26]3[c:27]2[CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]2)[c:35]([F:36])[cH:37]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C... | COc1ccc(COCCCO)cc1.Oc1nc2ncnn2c(C2CCCCCC2)c1-c1c(F)cc(F)cc1F | COc1ccc(COCCCOc2cc(F)c(-c3c(O)nc4ncnn4c3C3CCCCCC3)c(F)c2)cc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(COCCCOc2ccc(-c3cnc4ncnn4c3C3CCCCCC3)cc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 152.3 | [{"value": 152.3, "product": "C1(CCCCCC1)C1=C(C(=NC=2N1N=CN2)O)C2=C(C=C(C=C2F)OCCCOCC2=CC=C(C=C2)OC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 7-cycloheptyl-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-5-ol (362 mg, 1.0 mmol) and 3-[(4-methoxybenzyl)oxy]-1-propanol (490 mg, 2.5 mmol) in 4.0 mL of dimethylsulfoxide at room temperature is added sodium hydride (60% in mineral oil, 120 mg, 3.0 mmol). The mixture is stirred at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1cnc2ncnn2c1.C1CCCCCC1 | HF | CS(=O)C | null | 3 | COc1ccc(COCCCO)cc1.Oc1nc2ncnn2c(C2CCCCCC2)c1-c1c(F)cc(F)cc1F>CS(=O)C>COc1ccc(COCCCOc2cc(F)c(-c3c(O)nc4ncnn4c3C3CCCCCC3)c(F)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c65bec13f6af40bfa291e2b9ee177f76 | COc1ccc(COCCCOc2cc(F)c(-c3c(O)nc4ncnn4c3C3CCCCCC3)c(F)c2)cc1.O=P(Cl)(Cl)Cl>>COc1ccc(COCCCOc2cc(F)c(-c3c(Cl)nc4ncnn4c3C3CCCCCC3)c(F)c2)cc1 | C1(CCCCCC1)C1=C(C(=NC=2N1N=CN2)O)C2=C(C=C(C=C2F)OCCCOCC2=CC=C(C=C2)OC)F.P(=O)(Cl)(Cl)Cl.C(C)N(C1=CC=CC=C1)CC>>ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)OCCCOCC1=CC=C(C=C1)OC)F)C1CCCCCC1)N=CN2 | O[c:19]1[c:18](-[c:17]2[c:15]([F:16])[cH:14][c:13]([O:12][CH2:11][CH2:10][CH2:9][O:8][CH2:7][c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:39][cH:38]3)[cH:37][c:35]2[F:36])[c:27]([CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]2)[n:26]2[c:22]([n:21]1)[n:23][cH:24][n:25]2.O=P(Cl)(Cl)[Cl:20]>>[CH3:1][O:2][c:3]1[cH:4][c... | COc1ccc(COCCCOc2cc(F)c(-c3c(O)nc4ncnn4c3C3CCCCCC3)c(F)c2)cc1.O=P(Cl)(Cl)Cl | COc1ccc(COCCCOc2cc(F)c(-c3c(Cl)nc4ncnn4c3C3CCCCCC3)c(F)c2)cc1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | 0931592c624e33b002d2d3727976d0e1d5e44a0d838cefe4b8b67627403baf59 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(COCCCOc2ccc(-c3cnc4ncnn4c3C3CCCCCC3)cc2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7]:[#7;a:8]:2:[c:9](-[C:10]):[c:11]:1-[c:12]>>[C:10]-[c:9]1:[#7;a:8]2:[#7;a:7]:[c:6]:[#7;a:5]:[c:4]:2:[#7;a:3]:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:11]:1-[c:12] | null | [] | null | null | null | null | To the above 7-cycloheptyl-6-(2,6-difluoro-4-{3-[(4-methoxybenzyl)oxy]propoxy}phenyl)[1,2,4]triazolo[1,5-a]pyrimidin-5-ol (820 mg) is added 5 mL of phosphorous oxychloride and 2 mL of N,N-diethylaniline, and the mixture is heated at reflux for 1 h. The excess phosphorous oxychloride is removed in vaccuo, and the result... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cnc2ncnn2c1 | c1cnc2ncnn2c1 | c1ccccc1.c1ccccc1.c1cnc2ncnn2c1.C1CCCCCC1 | HCl | null | null | null | COc1ccc(COCCCOc2cc(F)c(-c3c(O)nc4ncnn4c3C3CCCCCC3)c(F)c2)cc1.O=P(Cl)(Cl)Cl>>COc1ccc(COCCCOc2cc(F)c(-c3c(Cl)nc4ncnn4c3C3CCCCCC3)c(F)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3649847cac1f4e6e99f14d8a98d7a75d | COc1ccc(COCCCOc2cc(F)c(-c3c(Cl)nc4ncnn4c3C3CCCCCC3)c(F)c2)cc1>>OCCCOc1cc(F)c(-c2c(Cl)nc3ncnn3c2C2CCCCCC2)c(F)c1 | ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)OCCCOCC1=CC=C(C=C1)OC)F)C1CCCCCC1)N=CN2.ClC=1C(C(=C(C(C1Cl)=O)C#N)C#N)=O>>ClC1=NC=2N(C(=C1C1=C(C=C(OCCCO)C=C1F)F)C1CCCCCC1)N=CN2 | COc1ccc(C[O:1][CH2:2][CH2:3][CH2:4][O:5][c:6]2[cH:7][c:8]([F:9])[c:10](-[c:11]3[c:12]([Cl:13])[n:14][c:15]4[n:16][cH:17][n:18][n:19]4[c:20]3[CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]3)[c:28]([F:29])[cH:30]2)cc1>>[OH:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([F:9])[c:10](-[c:11]2[c:12]([Cl:13])[n:14][c... | COc1ccc(COCCCOc2cc(F)c(-c3c(Cl)nc4ncnn4c3C3CCCCCC3)c(F)c2)cc1 | OCCCOc1cc(F)c(-c2c(Cl)nc3ncnn3c2C2CCCCCC2)c(F)c1 | null | null | O.C(Cl)Cl | Reduction | Cleavage of alkoxy ethers to alcohols | b9cb0e2e22c551f08401a6ebf7cca400a853b5888643e64a72f0d14fdf16154a | a4561cbdd42f56679299e19ea8b11070a39a15f6a95fb8a877e677f11b7ff57f | c1ccc(-c2cnc3ncnn3c2C2CCCCCC2)cc1 | C-O-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2]-[C:3]):c:c:1>>[C:3]-[C:2]-[OH;D1;+0:1] | 77.8 | [{"value": 77.8, "product": "ClC1=NC=2N(C(=C1C1=C(C=C(OCCCO)C=C1F)F)C1CCCCCC1)N=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 5-chloro-7-cycloheptyl-6-(2,6-difluoro-4-{3-[(4-methoxybenzyl)oxy]propoxy}phenyl)[1,2,4]triazolo[1,5-a]pyrimidine (56 mg, 0.1 mmol) in 4 mL of methylene chloride and 0.2 mL of water is added 2,3-dichloro-5,6-dicyano-1,4-bezoquinone (100 mg, 0.44 mmol). The mixture is stirred at room temperature for 20 ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol | c1ccccc1 | null | c1ccccc1.c1cnc2ncnn2c1.C1CCCCCC1 | HO- | O.C(Cl)Cl | null | 0.333333 | COc1ccc(COCCCOc2cc(F)c(-c3c(Cl)nc4ncnn4c3C3CCCCCC3)c(F)c2)cc1>O.C(Cl)Cl>OCCCOc1cc(F)c(-c2c(Cl)nc3ncnn3c2C2CCCCCC2)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ba1810bfcb95419989b90d1ac1d93088 | CN(CCCOc1cc(F)c(-c2c(O)nc3ncnn3c2C2CCCCCC2)c(F)c1)C(=O)OC(C)(C)C.O=P(Cl)(Cl)Cl>>CN(CCCOc1cc(F)c(-c2c(Cl)nc3ncnn3c2C2CCCCCC2)c(F)c1)C(=O)OC(C)(C)C | C1(CCCCCC1)C1=C(C(=NC=2N1N=CN2)O)C2=C(C=C(OCCCN(C(OC(C)(C)C)=O)C)C=C2F)F.P(=O)(Cl)(Cl)Cl.C(C)N(C1=CC=CC=C1)CC>>ClC1=NC=2N(C(=C1C1=C(C=C(OCCCN(C(OC(C)(C)C)=O)C)C=C1F)F)C1CCCCCC1)N=CN2 | O[c:13]1[c:12](-[c:11]2[c:9]([F:10])[cH:8][c:7]([O:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])[cH:31][c:29]2[F:30])[c:21]([CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[n:20]2[c:16]([n:15]1)[n:17][cH:18][n:19]2.O=P(Cl)(Cl)[Cl:14]>>[CH3:1][N:2]([CH2:3][CH2:4]... | CN(CCCOc1cc(F)c(-c2c(O)nc3ncnn3c2C2CCCCCC2)c(F)c1)C(=O)OC(C)(C)C.O=P(Cl)(Cl)Cl | CN(CCCOc1cc(F)c(-c2c(Cl)nc3ncnn3c2C2CCCCCC2)c(F)c1)C(=O)OC(C)(C)C | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | 0931592c624e33b002d2d3727976d0e1d5e44a0d838cefe4b8b67627403baf59 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2cnc3ncnn3c2C2CCCCCC2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7]:[#7;a:8]:2:[c:9](-[C:10]):[c:11]:1-[c:12]>>[C:10]-[c:9]1:[#7;a:8]2:[#7;a:7]:[c:6]:[#7;a:5]:[c:4]:2:[#7;a:3]:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:11]:1-[c:12] | null | [] | 90 | CELSIUS | null | null | To tert-butyl 3-[4-(7-cycloheptyl-5-hydroxy[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenoxy]propyl(methyl)carbamate (876 mg, 1.64 mmol) is added 5.8 mL of phosphorous oxychloride and 2.9 mL of N,N-diethylaniline, and the mixture is heated at 90° C. for 3 h. The excess phosphorous oxychloride is removed in vacc... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cnc2ncnn2c1 | c1cnc2ncnn2c1 | c1ccccc1.c1cnc2ncnn2c1.C1CCCCCC1 | HCl | null | 90 | null | CN(CCCOc1cc(F)c(-c2c(O)nc3ncnn3c2C2CCCCCC2)c(F)c1)C(=O)OC(C)(C)C.O=P(Cl)(Cl)Cl>>CN(CCCOc1cc(F)c(-c2c(Cl)nc3ncnn3c2C2CCCCCC2)c(F)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-94fdb62393a8470388014bda6354dcec | CN(CCCOc1cc(F)c(-c2c(Cl)nc3ncnn3c2C2CCCCCC2)c(F)c1)C(=O)OC(C)(C)C>>CNCCCOc1cc(F)c(-c2c(Cl)nc3ncnn3c2C2CCCCCC2)c(F)c1 | ClC1=NC=2N(C(=C1C1=C(C=C(OCCCN(C(OC(C)(C)C)=O)C)C=C1F)F)C1CCCCCC1)N=CN2.FC(C(=O)O)(F)F>>ClC1=NC=2N(C(=C1C1=C(C=C(OCCCNC)C=C1F)F)C1CCCCCC1)N=CN2.FC(C(=O)O)(F)F | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][c:9]([F:10])[c:11](-[c:12]2[c:13]([Cl:14])[n:15][c:16]3[n:17][cH:18][n:19][n:20]3[c:21]2[CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[c:29]([F:30])[cH:31]1>>[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][c:9]([F:10])[c:11](-[c:12]2[c:1... | CN(CCCOc1cc(F)c(-c2c(Cl)nc3ncnn3c2C2CCCCCC2)c(F)c1)C(=O)OC(C)(C)C | CNCCCOc1cc(F)c(-c2c(Cl)nc3ncnn3c2C2CCCCCC2)c(F)c1 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2cnc3ncnn3c2C2CCCCCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | 18 | HOUR | To a solution of tert-butyl 3-[4-(5-chloro-7-cycloheptyl [1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenoxy]propyl(methyl)carbamate (452 mg, 0.82 mmol) in 4 mL of methylene chloride is added 2.3 mL of trifluoroacetic acid. The mixture is stirred at room temperature for 18 h, and concentrated in vaccuo, yielding ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccccc1.c1cnc2ncnn2c1.C1CCCCCC1 | HO- | C(Cl)Cl | null | 18 | CN(CCCOc1cc(F)c(-c2c(Cl)nc3ncnn3c2C2CCCCCC2)c(F)c1)C(=O)OC(C)(C)C>C(Cl)Cl>CNCCCOc1cc(F)c(-c2c(Cl)nc3ncnn3c2C2CCCCCC2)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e3f93ad66dc84c42b016b81a12837149 | O=C(O)c1cc(Br)cnc1O.O=S(Cl)Cl>>O=C(O)c1cccnc1Cl | BrC=1C=NC(=C(C(=O)O)C1)O.S(=O)(Cl)Cl>>ClC1=C(C(=O)O)C=CC=N1 | O[c:9]1[c:4]([C:2](=[O:1])[OH:3])[cH:5][c:6](Br)[cH:7][n:8]1.O=S(Cl)[Cl:10]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[Cl:10] | O=C(O)c1cc(Br)cnc1O.O=S(Cl)Cl | O=C(O)c1cccnc1Cl | null | null | null | Functional Group Interconversion | OtherReaction | b61615ffa3205a9db4043261b57050bc62cd6c2df82599ac04be5637ae28995c | c82cc461af6e06935dddeb6b9f92147f67674f1d402fa9a7706939b230a523c5 | c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4](=[O;D1;H0:5])-[O;D1;H1:6]):[c;H0;D3;+0:7](-O):[#7;a:8]:[c:9]:1.Cl-S(=O)-[Cl;H0;D1;+0:10]>>[Cl;H0;D1;+0:10]-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9]:[cH;D2;+0:1]:[c:2]:[c:3]:1-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | null | [] | null | null | null | null | Substituted pyridines 12 can be prepared by the procedure described in Scheme 4. A solution of sodium hypobromite is freshly prepared and added to a 2-hydroxynicotinic acid 7 and heated, such as at a temperature of about 50° C. Additional sodium hypobromide may be added to form the bromo compound 8 as needed. The 5-bro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | Br- | null | null | null | O=C(O)c1cc(Br)cnc1O.O=S(Cl)Cl>>O=C(O)c1cccnc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2c94a1ace22b40abb15775032c237108 | O=[N+]([O-])c1ccc2c(Oc3n[nH]c4cc([N+](=O)[O-])ccc34)n[nH]c2c1>>Nc1ccc2c(Oc3n[nH]c4cc(N)ccc34)n[nH]c2c1 | [N+](=O)([O-])C1=CC=C2C(=NNC2=C1)OC1=NNC2=CC(=CC=C12)[N+](=O)[O-]>>NC1=CC=C2C(=NNC2=C1)OC1=NNC2=CC(=CC=C12)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[c:6]([O:7][c:8]3[n:9][nH:10][c:11]4[cH:12][c:13]([N+:14](=O)[O-])[cH:15][cH:16][c:17]34)[n:18][nH:19][c:20]2[cH:21]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([O:7][c:8]3[n:9][nH:10][c:11]4[cH:12][c:13]([NH2:14])[cH:15][cH:16][c:17]34)[n:18][nH:19][c:20]2[cH:21]1 | O=[N+]([O-])c1ccc2c(Oc3n[nH]c4cc([N+](=O)[O-])ccc34)n[nH]c2c1 | Nc1ccc2c(Oc3n[nH]c4cc(N)ccc34)n[nH]c2c1 | null | [Pd] | null | Reduction | OtherReaction | 6748a51a25102225412593c5a930e43f5a8904a80803177de025a6f83c59d65e | a303b0dfb15cc6bade463acf71681cf3ba7580b599dfa4d28d8caac83d08cd17 | c1ccc2c(Oc3n[nH]c4ccccc34)n[nH]c2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6].O=[N+;H0;D3:7](-[O-])-[c:8](:[c:9]):[c:10]:[c:11]:[#7;a:12]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3].[#7;a:12]:[c:11]:[c:10]:[c:8](-[NH2;D1;+0:7]):[c:9] | null | [] | null | null | null | null | Indazolyl ethers 38 can be prepared by the procedure described in Scheme 13. 6-Nitro-1H-2-hydroindazol-3-one 37 is protected such as with Boc2O and DMAP in CH2Cl2 at a temperature of about RT, to give the protected 6-nitro-2-hydroindazol-3-one. The protected 6-nitro-2-hydroindazol-3-one is reacted with an alcohol (wher... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group | Primary amine.Primary amine | null | null | c1ccc2n[nH]cc2c1.c1ccc2n[nH]cc2c1 | Other | [Pd] | null | null | O=[N+]([O-])c1ccc2c(Oc3n[nH]c4cc([N+](=O)[O-])ccc34)n[nH]c2c1>[Pd]>Nc1ccc2c(Oc3n[nH]c4cc(N)ccc34)n[nH]c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1587dd2df9244ca197ae4e1bfe91ec4e | O=[N+]([O-])N1CCc2ccccc21>>NN1CCc2ccccc21 | [N+](=O)([O-])N1CCC2=CC=CC=C12>>NN1CCC2=CC=CC=C12 | O=[N+:1]([O-])[N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]21>>[NH2:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]21 | O=[N+]([O-])N1CCc2ccccc21 | NN1CCc2ccccc21 | null | [Pd] | null | Reduction | Reduction of nitro groups to amines | 6bdc5b1d5c26702b9b2e2eba8a212ecfef1796cf7dff1d3c4aa29ea829bd6927 | 551d4b973c04e11a26a7d28f2bf46da71be13045335ec714830e5dd800ddb646 | c1ccc2c(c1)CCN2 | O=[N+;H0;D3:1](-[O-])-[#7:2](-[C:3])-[c:4]>>[C:3]-[#7:2](-[NH2;D1;+0:1])-[c:4] | null | [] | null | null | null | null | Substituted indolines 51 are prepared such as by the procedures described in Scheme 15. Substituted amino-indolines 48 are prepared from the nitroindoline 46 and a ketone in the presence of NaHB(OAc)3 to form the 1-substituted indoline 47. The nitroindoline 47 is hydrogenated, such as with H2 in the presence of a catal... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine | Hydrazine | null | null | c1ccc2c(c1)CC[NH]2 | Other | [Pd] | null | null | O=[N+]([O-])N1CCc2ccccc21>[Pd]>NN1CCc2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4f37722ccab48ea9c643fffa08d8fae | COc1cc([N+](=O)[O-])cc(C(F)(F)F)c1>>O=[N+]([O-])c1cc(O)cc(C(F)(F)F)c1 | COC1=CC(=CC(=C1)C(F)(F)F)[N+](=O)[O-].Cl.N1=CC=CC=C1>>[N+](=O)([O-])C=1C=C(C=C(C1)C(F)(F)F)O | C[O:7][c:6]1[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:14][c:9]([C:10]([F:11])([F:12])[F:13])[cH:8]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([OH:7])[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1 | COc1cc([N+](=O)[O-])cc(C(F)(F)F)c1 | O=[N+]([O-])c1cc(O)cc(C(F)(F)F)c1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 210 | CELSIUS | null | null | 1-Methoxy-3-nitro-5-trifluoromethyl-benzene (10 g, Aldrich) and pyridine-HCl (41.8 g, Aldrich) were mixed together and heated neat at 210° C. in an open flask. After 2.5 h the mixture was cooled to RT and partitioned between 1N HCl and EtOAc. The EtOAc fraction was washed with 1N HCl (4×), brine (1×), dried with Na2SO4... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | null | 210 | null | COc1cc([N+](=O)[O-])cc(C(F)(F)F)c1>>O=[N+]([O-])c1cc(O)cc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa7e02be9189472e85b9f9a365326929 | CC(C)(C)OC(=O)N1CCC(O)CC1.O=[N+]([O-])c1cc(O)cc(C(F)(F)F)c1>>CC(C)(C)OC(=O)N1CCC(Oc2cc([N+](=O)[O-])cc(C(F)(F)F)c2)CC1 | C(=O)(OC(C)(C)C)N1CCC(CC1)O.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[N+](=O)([O-])C=1C=C(C=C(C1)C(F)(F)F)O.CCOC(=O)/N=N/C(=O)OCC>>C(=O)(OC(C)(C)C)N1CCC(CC1)OC1=CC(=CC(=C1)C(F)(F)F)[N+](=O)[O-] | O[CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:27][CH2:26]1.[OH:12][c:13]1[cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][c:15]([N+:16](=[O:17... | CC(C)(C)OC(=O)N1CCC(O)CC1.O=[N+]([O-])c1cc(O)cc(C(F)(F)F)c1 | CC(C)(C)OC(=O)N1CCC(Oc2cc([N+](=O)[O-])cc(C(F)(F)F)c2)CC1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | a9e936b0e9135225700edbab1c7696738b7f1f0756494b6ceeeda63b184d572f | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccc(OC2CCNCC2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:10] | null | [] | -20 | CELSIUS | 8 | HOUR | 3-Nitro-5-trifluoromethyl-phenol (8.81 g) was dissolved in THF (76 ml). 1-Boc-4-hydroxy-piperidine (8.81 g, Aldrich) and Ph3P (11.15 g) were added and the solution was cooled to −20° C. A solution of DEAD (6.8 ml, Aldrich) in THF (36 ml) was added dropwise, maintaining the temperature between −20 and −10° C. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | HO- | C1CCOC1 | -20 | 8 | CC(C)(C)OC(=O)N1CCC(O)CC1.O=[N+]([O-])c1cc(O)cc(C(F)(F)F)c1>C1CCOC1>CC(C)(C)OC(=O)N1CCC(Oc2cc([N+](=O)[O-])cc(C(F)(F)F)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-db81e4b54a584baba88fec296194d0d9 | CC(C)(C)OC(=O)N1CCC(Oc2cc([N+](=O)[O-])cc(C(F)(F)F)c2)CC1>>CC(C)(C)OC(=O)N1CCC(Oc2cc(N)cc(C(F)(F)F)c2)CC1 | C(=O)(OC(C)(C)C)N1CCC(CC1)OC1=CC(=CC(=C1)C(F)(F)F)[N+](=O)[O-]>>C(=O)(OC(C)(C)C)N1CCC(CC1)OC1=CC(=CC(=C1)C(F)(F)F)N | O=[N+:16]([O-])[c:15]1[cH:14][c:13]([O:12][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:25][CH2:24]2)[cH:23][c:18]([C:19]([F:20])([F:21])[F:22])[cH:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][c:15]([NH2:16])[cH:17][c:18]([C... | CC(C)(C)OC(=O)N1CCC(Oc2cc([N+](=O)[O-])cc(C(F)(F)F)c2)CC1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(N)cc(C(F)(F)F)c2)CC1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(OC2CCNCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 1-Boc-4-(3-nitro-5-trifluoromethyl-phenoxy)-piperidine (470 mg) was dissolved in MeOH (12 ml) and Pd/C (10 mg) was added. After sparging briefly with H2, the mixture was stirred under H2 for 6H. The catalyst was removed by filtration and the MeOH solution was concentrated in vacuo to yield 1-Boc-4-(3-amino-5-trifluorom... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1CC[NH]CC1.c1ccccc1 | Other | [Pd].CO | null | null | CC(C)(C)OC(=O)N1CCC(Oc2cc([N+](=O)[O-])cc(C(F)(F)F)c2)CC1>[Pd].CO>CC(C)(C)OC(=O)N1CCC(Oc2cc(N)cc(C(F)(F)F)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a950f58865714d7fa987025e113fc383 | CC(C)(C)OC(=O)N1CCC(Oc2cc(N)cc(C(F)(F)F)c2)CC1.O=C(Cl)c1cccnc1F>>CC(C)(C)OC(=O)N1CCC(Oc2cc(NC(=O)c3cccnc3F)cc(C(F)(F)F)c2)CC1 | CCOC(=O)C.CCCCCC.C(=O)(O)[O-].[Na+].C(=O)(OC(C)(C)C)N1CCC(CC1)OC1=CC(=CC(=C1)C(F)(F)F)N.FC1=NC=CC=C1C(=O)Cl>>C(=O)(OC(C)(C)C)N1CCC(CC1)OC1=CC(=CC(=C1)C(F)(F)F)NC(=O)C=1C(=NC=CC1)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][c:15]([NH2:16])[cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]2)[CH2:33][CH2:34]1.Cl[C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][c:24]1[F:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C... | CC(C)(C)OC(=O)N1CCC(Oc2cc(N)cc(C(F)(F)F)c2)CC1.O=C(Cl)c1cccnc1F | CC(C)(C)OC(=O)N1CCC(Oc2cc(NC(=O)c3cccnc3F)cc(C(F)(F)F)c2)CC1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1cccc(OC2CCNCC2)c1)c1cccnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[F;D1;H0:6]):[#7;a:7]:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[F;D1;H0:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:4] | null | [] | null | null | 2.5 | HOUR | 1-Boc-4-(3-amino-5-trifluoromethyl-phenoxy)-piperidine (4.37 g) was dissolved in CH2Cl2 (100 ml) and NaHCO3 (2.4 g, Baker) was added. 2-Fluoropyridine-3-carbonyl chloride (2.12 g) was added an the reaction was stirred at RT for 2.5 h. The reaction was filtered and concentrated in vacuo to yield a yellow foam. (30%) EtO... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccccc1.c1ccncc1 | HCl | C(Cl)Cl | null | 2.5 | CC(C)(C)OC(=O)N1CCC(Oc2cc(N)cc(C(F)(F)F)c2)CC1.O=C(Cl)c1cccnc1F>C(Cl)Cl>CC(C)(C)OC(=O)N1CCC(Oc2cc(NC(=O)c3cccnc3F)cc(C(F)(F)F)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4d55ad2ea91547f6954487c0bae278e1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(N)cc(C(F)(F)F)c2)CC1.O=C(Cl)c1cccnc1Cl>>CC(C)(C)OC(=O)N1CCC(Oc2cc(NC(=O)c3cccnc3Cl)cc(C(F)(F)F)c2)CC1 | C(=O)(OC(C)(C)C)N1CCC(CC1)OC1=CC(=CC(=C1)C(F)(F)F)N.ClC1=NC=CC=C1C(=O)Cl.C(=O)(OC(C)(C)C)N1CCC(CC1)OC1=CC(=CC(=C1)C(F)(F)F)NC(=O)C=1C(=NC=CC1)F>>C(=O)(OC(C)(C)C)N1CCC(CC1)OC1=CC(=CC(=C1)C(F)(F)F)NC(=O)C=1C(=NC=CC1)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][c:15]([NH2:16])[cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]2)[CH2:33][CH2:34]1.Cl[C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][c:24]1[Cl:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][... | CC(C)(C)OC(=O)N1CCC(Oc2cc(N)cc(C(F)(F)F)c2)CC1.O=C(Cl)c1cccnc1Cl | CC(C)(C)OC(=O)N1CCC(Oc2cc(NC(=O)c3cccnc3Cl)cc(C(F)(F)F)c2)CC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1cccc(OC2CCNCC2)c1)c1cccnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:4] | null | [] | null | null | null | null | 1-Boc-4-{3-[(2-chloro-pyridine-3-carbonyl)-amino]-5-trifluoromethyl-phenoxy}-piperidine was prepared from 1-Boc-4-(3-amino-5-trifluoromethyl-phenoxy)-piperidine and 2-chloropyridine-3-carbonyl chloride by a procedure similar to that described in the preparation of 1-Boc-4-{3-[(2-fluoro-pyridine-3-carbonyl)-amino]-5-tri... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccccc1.c1ccncc1 | HCl | null | null | null | CC(C)(C)OC(=O)N1CCC(Oc2cc(N)cc(C(F)(F)F)c2)CC1.O=C(Cl)c1cccnc1Cl>>CC(C)(C)OC(=O)N1CCC(Oc2cc(NC(=O)c3cccnc3Cl)cc(C(F)(F)F)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-facb0e23ce574bfe9a9cd300c9825163 | CC(C)(C)OC(=O)N1CCC(Oc2cc(NC(=O)c3cccnc3F)cc(C(F)(F)F)c2)CC1.CC(C)(C)OC(=O)N1CCCC1COc1cc(N)cc(C(F)(F)F)c1>>CC(C)(C)OC(=O)N1CCCC1COc1cc(NC(=O)c2cccnc2F)cc(C(F)(F)F)c1 | C(=O)(OC(C)(C)C)N1CCC(CC1)OC1=CC(=CC(=C1)C(F)(F)F)NC(=O)C=1C(=NC=CC1)F.C(=O)(OC(C)(C)C)N1C(CCC1)COC1=CC(=CC(=C1)C(F)(F)F)N>>C(=O)(OC(C)(C)C)N1C(CCC1)COC1=CC(=CC(=C1)C(F)(F)F)NC(=O)C=1C(=NC=CC1)F | CC(C)(C)OC(=O)N1CCC(Oc2cc(N[C:19](=[O:20])[c:21]3[cH:22][cH:23][cH:24][n:25][c:26]3[F:27])cc(C(F)(F)F)c2)CC1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:13][O:14][c:15]1[cH:16][c:17]([NH2:18])[cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34]1>>[CH3:1][C:2]([CH3:3])([CH3:4]... | CC(C)(C)OC(=O)N1CCC(Oc2cc(NC(=O)c3cccnc3F)cc(C(F)(F)F)c2)CC1.CC(C)(C)OC(=O)N1CCCC1COc1cc(N)cc(C(F)(F)F)c1 | CC(C)(C)OC(=O)N1CCCC1COc1cc(NC(=O)c2cccnc2F)cc(C(F)(F)F)c1 | null | null | null | Acylation | OtherReaction | 4a154f3d0451f7adc7e06eb20420593d6aae77ff8199bbf6d044af104e3f431a | 3a1146f373e13aeeb4978d04787fef10d7913789488cc4629f5b8b7a8a42f296 | O=C(Nc1cccc(OCC2CCCN2)c1)c1cccnc1 | C-C(-C)(-C)-O-C(=O)-N1-C-C-C(-O-c2:c:c(-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[F;D1;H0:6]):[#7;a:7]:[c:8]):c:c(-C(-F)(-F)-F):c:2)-C-C-1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[F;D1;H0:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:4] | null | [] | null | null | null | null | 1-Boc-2-{3-[(2-Fluoro-pyridine-3-carbonyl)-amino]-5-trifluoromethyl-phenoxymethyl}-pyrrolidine was prepared from 1-Boc-2-(3-amino-5-trifluoromethyl-phenoxymethyl)-pyrrolidine by a procedure similar to that described in the preparation of 1-Boc-4-{3-[(2-fluoro-pyridine-3-carbonyl)-amino]-5-trifluoromethyl-phenoxy}-piper... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carbamic ester.Ether.Ether.Secondary amide.Primary amine.Boc | Secondary amide | C1CCNCC1.c1ccccc1 | null | C1CC[NH]C1.c1ccccc1.c1ccncc1 | HF | null | null | null | CC(C)(C)OC(=O)N1CCC(Oc2cc(NC(=O)c3cccnc3F)cc(C(F)(F)F)c2)CC1.CC(C)(C)OC(=O)N1CCCC1COc1cc(N)cc(C(F)(F)F)c1>>CC(C)(C)OC(=O)N1CCCC1COc1cc(NC(=O)c2cccnc2F)cc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5acee4ef974a4b6c981b26380a571c62 | CC(C)(C)OC(=O)N1CCCC1COc1cc([N+](=O)[O-])cc(C(F)(F)F)c1>>O=[N+]([O-])c1cc(OCC2CCCN2)cc(C(F)(F)F)c1 | C(=O)(OC(C)(C)C)N1C(CCC1)COC1=CC(=CC(=C1)C(F)(F)F)[N+](=O)[O-].C(=O)(C(F)(F)F)O>>[N+](=O)([O-])C=1C=C(OCC2NCCC2)C=C(C1)C(F)(F)F | CC(C)(C)OC(=O)[N:13]1[CH:9]([CH2:8][O:7][c:6]2[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:20][c:15]([C:16]([F:17])([F:18])[F:19])[cH:14]2)[CH2:10][CH2:11][CH2:12]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([O:7][CH2:8][CH:9]2[CH2:10][CH2:11][CH2:12][NH:13]2)[cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]1 | CC(C)(C)OC(=O)N1CCCC1COc1cc([N+](=O)[O-])cc(C(F)(F)F)c1 | O=[N+]([O-])c1cc(OCC2CCCN2)cc(C(F)(F)F)c1 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | 7b506000be0005f6be41b2386b5bd6a8c45f704baa22d692d2f2ec984758e4ad | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(OCC2CCCN2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6]>>[C:6]-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | 1 | HOUR | 1-Boc-2-(3-nitro-5-trifluoromethyl-phenoxymethyl)-pyrrolidine (2.35 g) was dissolved in CH2Cl2 (60 ml) and TFA (20 ml) was added. After stirring for 1 h at RT, the mixture was concentrated in vacuo to yield 2-(3-nitro-5-trifluoromethyl-phenoxymethyl)-pyrrolidine as an oil that solidified upon standing. The material was... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | c1ccccc1.C1CCNC1 | HO- | C(Cl)Cl | null | 1 | CC(C)(C)OC(=O)N1CCCC1COc1cc([N+](=O)[O-])cc(C(F)(F)F)c1>C(Cl)Cl>O=[N+]([O-])c1cc(OCC2CCCN2)cc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a424300cf364497ebc9bd7e8f2623081 | C=O.O=[N+]([O-])c1cc(OCC2CCCN2)cc(C(F)(F)F)c1>>CN1CCCC1COc1cc([N+](=O)[O-])cc(C(F)(F)F)c1 | CC(=O)O.C=O.[N+](=O)([O-])C=1C=C(OCC2NCCC2)C=C(C1)C(F)(F)F.[BH3-]C#N.[Na+]>>CN1C(CCC1)COC1=CC(=CC(=C1)C(F)(F)F)[N+](=O)[O-] | O=[CH2:1].[NH:2]1[CH2:3][CH2:4][CH2:5][CH:6]1[CH2:7][O:8][c:9]1[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]1[CH2:7][O:8][c:9]1[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]1 | C=O.O=[N+]([O-])c1cc(OCC2CCCN2)cc(C(F)(F)F)c1 | CN1CCCC1COc1cc([N+](=O)[O-])cc(C(F)(F)F)c1 | null | null | CC#N | Functional Group Addition | Eschweiler-Clarke Secondary Amine Methylation | 596806345838051e870a8f6bc98ea80fe70c98a5e33506938d4dd972c4e2862a | 68e600b2a07b08da0e807cdaeea0a42b844f72be0a4c3ae081bd557e5f2bfd2d | c1ccc(OCC2CCCN2)cc1 | O=[CH2;D1;+0:1].[C:2]-[C:3]1-[C:4]-[C:5]-[C:6]-[NH;D2;+0:7]-1>>[C:2]-[C:3]1-[C:4]-[C:5]-[C:6]-[N;H0;D3;+0:7]-1-[CH3;D1;+0:1] | null | [] | null | null | 45 | MINUTE | 2-(3-Nitro-5-trifluoromethyl-phenoxymethyl)-pyrrolidine (6 mmol) was dissolved in CH3CN (20 ml) and formaldehyde (2.4 ml, 37% aqueous) was added. NaBH3CN (607 mg) was added, an exotherm was observed. The pH is monitored every 15 min and adjusted to ˜7 with AcOH. After 45 min, the mixture was concentrated in vacuo and t... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | Other | CC#N | null | 0.75 | C=O.O=[N+]([O-])c1cc(OCC2CCCN2)cc(C(F)(F)F)c1>CC#N>CN1CCCC1COc1cc([N+](=O)[O-])cc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-79e9e6ff8dd14b82b6e33e56e284dd72 | CC(C)(C)c1ccc([N+](=O)[O-])cc1[N+](=O)[O-]>>CC(C)(C)c1ccc(N)cc1[N+](=O)[O-] | [S].[N+](=O)([O-])C1=CC(=C(C=C1)C(C)(C)C)[N+](=O)[O-]>>C(C)(C)(C)C1=C(C=C(C=C1)N)[N+](=O)[O-] | O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[c:11]([N+:12](=[O:13])[O-:14])[cH:10]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:10][c:11]1[N+:12](=[O:13])[O-:14] | CC(C)(C)c1ccc([N+](=O)[O-])cc1[N+](=O)[O-] | CC(C)(C)c1ccc(N)cc1[N+](=O)[O-] | null | null | O | Functional Group Interconversion | Reduction of nitro groups to amines | 5c1ea979989295c14f1f65f49e58974d5c524451abca65fc2e6cec44e3d0784f | 10b8579fd1662beac4350d758bc16e1f45ee6ea295ff9572db62110c9e2a77db | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of 1,3-dinitro-4-tert-butylbenzene (10.0 g) in H2O (56 ml) was heated to reflux. A mixture of Na2S (21.42 g) and sulfur (2.85 g) in H2O (34 ml) was added over 1 h via an addition funnel. The reaction maintained at reflux for 1.5 h then cooled to RT and extracted with EtOAc. The organic extracts were combined ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | O | null | null | CC(C)(C)c1ccc([N+](=O)[O-])cc1[N+](=O)[O-]>O>CC(C)(C)c1ccc(N)cc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6889494b13bd4ce1a70acbee562ea485 | CC(=O)OC(C)=O.Nc1cc(Br)cc(C(F)(F)F)c1>>CC(=O)Nc1cc(Br)cc(C(F)(F)F)c1 | BrC=1C=C(C=C(C1)C(F)(F)F)N.CC(=O)OC(=O)C.O>>BrC=1C=C(C=C(C1)C(F)(F)F)NC(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][c:7]([Br:8])[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([Br:8])[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1 | CC(=O)OC(C)=O.Nc1cc(Br)cc(C(F)(F)F)c1 | CC(=O)Nc1cc(Br)cc(C(F)(F)F)c1 | null | null | CC(=O)O | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 8 | HOUR | 3-Bromo-5-(trifluoromethyl)phenylamine (5 g, Alfa-Aesar) was dissolved in AcOH (140 ml) and Ac2O (5.9 ml, Aldrich) was added. The reaction was stirred at RT overnight. The mixture was added slowly to H2O (˜700 ml) forming a white precipitate. The solid was isolated by filtration, washed with H2O and dried under vacuum ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | CC(=O)O | null | 8 | CC(=O)OC(C)=O.Nc1cc(Br)cc(C(F)(F)F)c1>CC(=O)O>CC(=O)Nc1cc(Br)cc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4d1ba4a1429b456fb24b0ac71be3ca02 | CC(=O)Nc1cc(CCCN2CCCCC2)cc(C(F)(F)F)c1>>Nc1cc(CCCN2CCCCC2)cc(C(F)(F)F)c1 | N1(CCCCC1)CCCC=1C=C(C=C(C1)C(F)(F)F)NC(C)=O.Cl>>N1(CCCCC1)CCCC=1C=C(C=C(C1)C(F)(F)F)N | CC(=O)[NH:1][c:2]1[cH:3][c:4]([CH2:5][CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]1>>[NH2:1][c:2]1[cH:3][c:4]([CH2:5][CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]1 | CC(=O)Nc1cc(CCCN2CCCCC2)cc(C(F)(F)F)c1 | Nc1cc(CCCN2CCCCC2)cc(C(F)(F)F)c1 | null | null | CCO | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc(CCCN2CCCCC2)cc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 70 | CELSIUS | 8 | HOUR | N-[3-(3-Piperidin-1-yl-propyl)-5-trifluoromethyl-phenyl]-acetamide (1.33 g) was dissolved in EtOH (40 ml) and 12 N HCl (40 ml) was added. After stirring overnight at 70° C. and RT, the mixture was concentrated in vacuo, affording 3-(3-piperidin-1-yl-propyl)-5-trifluoromethyl-phenylamine as a brown oil.
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1.C1CC[NH]CC1 | HO- | CCO | 70 | 8 | CC(=O)Nc1cc(CCCN2CCCCC2)cc(C(F)(F)F)c1>CCO>Nc1cc(CCCN2CCCCC2)cc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-12d9fdeda79849ceaaead73b998a6d10 | CC(C)(C)OC(=O)N1CCC(CN2CC(C)(C)c3ccc([N+](=O)[O-])cc32)CC1>>CC1(C)CN(CC2CCNCC2)c2cc([N+](=O)[O-])ccc21 | CC1(CN(C2=CC(=CC=C12)[N+](=O)[O-])CC1CCN(CC1)C(=O)OC(C)(C)C)C>>CC1(CN(C2=CC(=CC=C12)[N+](=O)[O-])CC1CCNCC1)C | CC(C)(C)OC(=O)[N:10]1[CH2:9][CH2:8][CH:7]([CH2:6][N:5]2[CH2:4][C:2]([CH3:1])([CH3:3])[c:21]3[c:13]2[cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]3)[CH2:12][CH2:11]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[c:13]2[cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20][... | CC(C)(C)OC(=O)N1CCC(CN2CC(C)(C)c3ccc([N+](=O)[O-])cc32)CC1 | CC1(C)CN(CC2CCNCC2)c2cc([N+](=O)[O-])ccc21 | null | null | Cl.CCOC(=O)C | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc2c(c1)CCN2CC1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | null | [] | null | null | 2 | HOUR | 3,3-Dimethyl-1-(1-Boc-piperidin-4-ylmethyl)-6-nitro-2,3-dihydro-1H-indole was dissolved in HCl/EtOAc and stirred for 2 h. The mixture was concentrated in vacuo and partitioned between 1,2-dichloroethane and 1N NaOH. The organic layer was removed, washed with brine, dried (Na2SO4) and filtered. The material was used wit... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccc2c(c1)CC[NH]2 | HO- | Cl.CCOC(=O)C | null | 2 | CC(C)(C)OC(=O)N1CCC(CN2CC(C)(C)c3ccc([N+](=O)[O-])cc32)CC1>Cl.CCOC(=O)C>CC1(C)CN(CC2CCNCC2)c2cc([N+](=O)[O-])ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ea737714a754007ad2eb13654ea3835 | C=CCN1CCOCC1.CC(=O)Nc1cc(Br)cc(C(F)(F)F)c1>>CC(=O)Nc1cc(CCCN2CCOCC2)cc(C(F)(F)F)c1 | C(C=C)N1CCOCC1.BrC=1C=C(C=C(C1)C(F)(F)F)NC(C)=O.N1(CCCCC1)CCCC=1C=C(C=C(C1)C(F)(F)F)NC(C)=O>>N1(CCOCC1)CCCC=1C=C(C=C(C1)C(F)(F)F)NC(C)=O | [CH2:8]=[CH:9][CH2:10][N:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1.Br[c:7]1[cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:23][c:18]([C:19]([F:20])([F:21])[F:22])[cH:17]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[cH:17][c:18]([C:19]([F:20])([F:21])[F... | C=CCN1CCOCC1.CC(=O)Nc1cc(Br)cc(C(F)(F)F)c1 | CC(=O)Nc1cc(CCCN2CCOCC2)cc(C(F)(F)F)c1 | null | null | null | C-C Coupling | OtherReaction | 2d4a44695e29e4a9ab430c3b66736ad86dd99247e7216f16f3ca137abca78747 | df8442c9f2045421fb18548edb9c6acaeb9710f63e741d9f72e0000ca35c948a | c1ccc(CCCN2CCOCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]-[C:7]-[CH;D2;+0:8]=[CH2;D1;+0:9]>>[#7:6]-[C:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | N-[3-(3-Morpholin-4-yl-propyl)-5-trifluoromethyl-phenyl]-acetamide was prepared from allyl morpholine and N-(3-bromo-5-trifluoromethyl-phenyl)-acetamide similar to that described in the preparation of N-[3-(3-piperidin-1-yl-propyl)-5-trifluoromethyl-phenyl]-acetamide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Allyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1.C1COCC[NH]1 | Br- | null | null | null | C=CCN1CCOCC1.CC(=O)Nc1cc(Br)cc(C(F)(F)F)c1>>CC(=O)Nc1cc(CCCN2CCOCC2)cc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bc47abb28d8643fba69d2f56ca33e44d | CC(=O)Nc1cc(CCCN2CCOCC2)cc(C(F)(F)F)c1>>Nc1cc(CCCN2CCOCC2)cc(C(F)(F)F)c1 | N1(CCCCC1)CCCC=1C=C(C=C(C1)C(F)(F)F)N.N1(CCOCC1)CCCC=1C=C(C=C(C1)C(F)(F)F)NC(C)=O>>N1(CCOCC1)CCCC=1C=C(C=C(C1)C(F)(F)F)N | CC(=O)[NH:1][c:2]1[cH:3][c:4]([CH2:5][CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]1>>[NH2:1][c:2]1[cH:3][c:4]([CH2:5][CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]1 | CC(=O)Nc1cc(CCCN2CCOCC2)cc(C(F)(F)F)c1 | Nc1cc(CCCN2CCOCC2)cc(C(F)(F)F)c1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc(CCCN2CCOCC2)cc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 3-(3-Morpholin-4-yl-propyl)-5-trifluoromethyl-phenylamine was prepared from N-[3-(3-morpholin-4-yl-propyl)-5-trifluoromethyl-phenyl]-acetamide similar to that described in the preparation of 3-(3-piperidin-1-yl-propyl)-5-trifluoromethyl-phenylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1.C1COCC[NH]1 | HO- | null | null | null | CC(=O)Nc1cc(CCCN2CCOCC2)cc(C(F)(F)F)c1>>Nc1cc(CCCN2CCOCC2)cc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1dd9fcd5907c45d0a728a79c728f030c | C=C1CCN(C)CC1.CC(=O)Nc1cc(Br)cc(C(F)(F)F)c1>>CC(=O)Nc1cc(C2CCN(C)CC2)cc(C(F)(F)F)c1 | CN1CCC(CC1)=C.BrC=1C=C(C=C(C1)C(F)(F)F)NC(C)=O.N1(CCCCC1)CCCC=1C=C(C=C(C1)C(F)(F)F)NC(C)=O>>CN1CCC(CC1)C=1C=C(C=C(C1)C(F)(F)F)NC(C)=O | C=[C:8]1[CH2:9][CH2:10][N:11]([CH3:12])[CH2:13][CH2:14]1.Br[c:7]1[cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:21][c:16]([C:17]([F:18])([F:19])[F:20])[cH:15]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([CH:8]2[CH2:9][CH2:10][N:11]([CH3:12])[CH2:13][CH2:14]2)[cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]1 | C=C1CCN(C)CC1.CC(=O)Nc1cc(Br)cc(C(F)(F)F)c1 | CC(=O)Nc1cc(C2CCN(C)CC2)cc(C(F)(F)F)c1 | null | null | null | C-C Coupling | OtherReaction | 993479cf39c04983afa148c3c4a2c6e5a7ee5fe5faa129754f7d6a55323bb504 | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | c1ccc(C2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C=[C;H0;D3;+0:6]1-[C:7]-[C:8]-[#7:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[CH;D3;+0:6]1-[C:7]-[C:8]-[#7:9]-[C:10]-[C:11]-1):[c:4]:[c:5] | null | [] | null | null | null | null | N-[3-(1-Methylpiperidin-4-yl)-5-trifluoromethyl-phenyl]-acetamide was prepared from 1-methyl-4-methylene-piperidine and N-(3-bromo-5-trifluoromethyl-phenyl)-acetamide similar to that described in the preparation of N-[3-(3-piperidin-1-yl-propyl)-5-trifluoromethyl-phenyl]-acetamide.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | C1CC[NH]CC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HBr | null | null | null | C=C1CCN(C)CC1.CC(=O)Nc1cc(Br)cc(C(F)(F)F)c1>>CC(=O)Nc1cc(C2CCN(C)CC2)cc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ba17c1c4d7f743a0b43c6abc06e718a6 | CC(=O)Nc1cc(C2CCN(C)CC2)cc(C(F)(F)F)c1>>CN1CCC(c2cc(N)cc(C(F)(F)F)c2)CC1 | N1(CCCCC1)CCCC=1C=C(C=C(C1)C(F)(F)F)N.CN1CCC(CC1)C=1C=C(C=C(C1)C(F)(F)F)NC(C)=O>>CN1CCC(CC1)C=1C=C(C=C(C1)C(F)(F)F)N | CC(=O)[NH:9][c:8]1[cH:7][c:6]([CH:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:18][CH2:17]2)[cH:16][c:11]([C:12]([F:13])([F:14])[F:15])[cH:10]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([c:6]2[cH:7][c:8]([NH2:9])[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]2)[CH2:17][CH2:18]1 | CC(=O)Nc1cc(C2CCN(C)CC2)cc(C(F)(F)F)c1 | CN1CCC(c2cc(N)cc(C(F)(F)F)c2)CC1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc(C2CCNCC2)cc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 3-(1-Methylpiperidin-4-yl)-5-trifluoromethyl-phenylamine was prepared from N-[3-(1-methylpiperidin-4-yl)-5-trifluoromethyl-phenyl]-acetamide similar to the procedure described in the preparation of 3-(3-piperidin-1-yl-propyl)-5-trifluoromethyl-phenylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | C1CC[NH]CC1.c1ccccc1 | HO- | null | null | null | CC(=O)Nc1cc(C2CCN(C)CC2)cc(C(F)(F)F)c1>>CN1CCC(c2cc(N)cc(C(F)(F)F)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eaf46af33faf4d5d97da5970b4ed4fac | Cl>>Cl.Cl | CN1CCC(CC1)OC1=NC=CC(=C1)CN.Cl.CCOCC>>Cl.Cl.CN1CCC(CC1)OC1=NC=CC(=C1)CN | [ClH:17]>>[ClH:17].[ClH:18] | Cl | Cl.Cl | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | [2-(1-Methylpiperidin-4-yloxy)-pyridin-4-yl]methylamine was diluted with Et2O (50 ml) and 1M HCl/Et2O (47 ml) was added. The vessel was swirled until precipitate formed.
Conditions: See reaction.notes.procedure_details.
Workup: was added; formed | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | CCOCC | null | null | Cl>CCOCC>Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-35c523bdd80c45beba839f8536d196ec | COC(=O)C(C)N1CCOCC1>>CC(CO)N1CCOCC1 | [OH-].[Na+].[H-].[H-].[H-].[H-].[Li+].[Al+3].N#N.N1(CCOCC1)C(C(=O)OC)C>>N1(CCOCC1)C(CO)C | CO[C:3]([CH:2]([CH3:1])[N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)=[O:4]>>[CH3:1][CH:2]([CH2:3][OH:4])[N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1 | COC(=O)C(C)N1CCOCC1 | CC(CO)N1CCOCC1 | null | null | O.C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1COCCN1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[#7:4])-[C;D1;H3:5]>>[#7:4]-[C:3](-[C;D1;H3:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | 0 | CELSIUS | 1 | HOUR | LAH powder (1.6 g) was added to a flask while under N2 atmosphere, immediately followed by THF (50 ml). The mixture was chilled to 0° C., methyl 2-morpholin-4-yl-propionate (5 g) was added dropwise to the reaction mixture and stirred at 0° C. After 1 h, the mixture was worked up by adding H2O (44 mL), 2N NaOH (44 mL), ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1COCC[NH]1 | Other | O.C1CCOC1 | 0 | 1 | COC(=O)C(C)N1CCOCC1>O.C1CCOC1>CC(CO)N1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a350655571c24bc38bae786d41339d9c | CC(C)(C)c1ccccc1N.O=[N+]([O-])[O-]>>CC(C)(C)c1ccc([N+](=O)[O-])cc1N | [N+](=O)([O-])[O-].[K+].OS(=O)(=O)O.C(C)(C)(C)C1=C(N)C=CC=C1.[N+](=O)([O-])[O-].[K+].BrC1=C(C(=O)N)C=CC=N1>>C(C)(C)(C)C1=C(N)C=C(C=C1)[N+](=O)[O-] | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][cH:8][cH:12][c:13]1[NH2:14].[O-][N+:9](=[O:10])[O-:11]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[NH2:14] | CC(C)(C)c1ccccc1N.O=[N+]([O-])[O-] | CC(C)(C)c1ccc([N+](=O)[O-])cc1N | null | null | O | Functional Group Addition | Aromatic nitration with NO3 salt | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | [O-]-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | -10 | CELSIUS | null | null | To H2SO4 (98%, 389 mL) in a 500 mL 3-neck flask was added 2-tert-butyl aniline (40.6 mL). The reaction was cooled to −10° C. and KNO3 in 3.89 g aliquots was added every 6 min for a total of 10 aliquots. Tried to maintain temperature at −5° C. to −10° C. After final addition of KNO3, stirred the reaction for five min th... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | O | -10 | null | CC(C)(C)c1ccccc1N.O=[N+]([O-])[O-]>O>CC(C)(C)c1ccc([N+](=O)[O-])cc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-87e7bf417e8b4a33a1f5548ab4869f94 | CC(C)(C)c1ccc([N+](=O)[O-])cc1N.O=S(=O)(O)O>>CC(C)(C)c1ccc([N+](=O)[O-])cc1O | OS(=O)(=O)O.C(C)(C)(C)C1=C(N)C=C(C=C1)[N+](=O)[O-].NC1=CC=CC=C1.NC(=O)N.N(=O)[O-].[Na+].N(=O)[O-].[Na+]>>C(C)(C)(C)C1=C(C=C(C=C1)[N+](=O)[O-])O | N[c:13]1[c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12]1.O=S(=O)(O)[OH:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[OH:14] | CC(C)(C)c1ccc([N+](=O)[O-])cc1N.O=S(=O)(O)O | CC(C)(C)c1ccc([N+](=O)[O-])cc1O | null | null | O.CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | ea88ed7f3099519cddf317836afa8700324714e983b7b91a9a2b5fa238ea7972 | 0faab53fb44f5d790c940e8273c888214a6763f53a41b0c03d0241319b9333e9 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].O-S(=O)(=O)-[OH;D1;+0:7]>>[C:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[OH;D1;+0:7]):[c:2]:[c:3] | null | [] | 0 | CELSIUS | null | null | In a 250 ml round bottom flask, 20 mL concentrated H2SO4 was added to 2-tert-butyl-5-nitro-aniline (7.15 g) by adding 5 mL aliquots of acid and sonicating with occasional heating until all of the starting aniline went into solution. H2O (84 ml) was added with stirring, then the reaction was cooled to 0° C. forming a ye... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | O.CCOC(=O)C | 0 | null | CC(C)(C)c1ccc([N+](=O)[O-])cc1N.O=S(=O)(O)O>O.CCOC(=O)C>CC(C)(C)c1ccc([N+](=O)[O-])cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-518f6a5655754bf0a29299adb7606654 | C=O.CCOC(=O)C1CCNCC1>>CCOC(=O)C1CCN(C)CC1 | [BH3-]C#N.[Na+].C=O.C(C)(=O)O.C(C)OC(=O)C1CCNCC1>>C(C)OC(=O)C1CCN(CC1)C | O=[CH2:10].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][NH:9][CH2:11][CH2:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][CH2:12]1 | C=O.CCOC(=O)C1CCNCC1 | CCOC(=O)C1CCN(C)CC1 | null | null | CO | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | e23db47f33553519e7237e30c3b19a21fcbb90bde44fbb5566021920bc9b7164 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | C1CCNCC1 | O=[CH2;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[C:5]-[C:6] | null | [] | 0 | CELSIUS | 2 | HOUR | Piperidine-4-carboxylic acid ethyl ester (78 g) was dissolved in MeOH (1.2 L) at RT then formaldehyde (37%, 90 ml) and acetic acid (42 ml) were added and stirred for 2 h. The mixture was cooled to 0° C., NaCNBH3 (70 g) was added, and the mix was stirred for 20 min at 0° C., then overnight at RT. The mixture was cooled ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | Other | CO | 0 | 2 | C=O.CCOC(=O)C1CCNCC1>CO>CCOC(=O)C1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b0dfe7bd1633448ea55de33fb70307fb | CC(C)(C)OC(=O)N1CCC(Oc2cc(NC(=O)c3cccnc3Cl)cc(C(F)(F)F)c2)CC1.CN1CCC(COc2cc(N)ccc2C(C)(C)C)CC1>>CN1CCC(COc2cc(NC(=O)c3cccnc3Cl)ccc2C(C)(C)C)CC1 | C(=O)(OC(C)(C)C)N1CCC(CC1)OC1=CC(=CC(=C1)C(F)(F)F)NC(=O)C=1C(=NC=CC1)Cl.C(C)(C)(C)C1=C(C=C(C=C1)N)OCC1CCN(CC1)C>>C(C)(C)(C)C1=C(C=C(C=C1)NC(C1=C(N=CC=C1)Cl)=O)OCC1CCN(CC1)C | CC(C)(C)OC(=O)N1CCC(Oc2cc(N[C:12](=[O:13])[c:14]3[cH:15][cH:16][cH:17][n:18][c:19]3[Cl:20])cc(C(F)(F)F)c2)CC1.[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:6][O:7][c:8]2[cH:9][c:10]([NH2:11])[cH:21][cH:22][c:23]2[C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:6][O:7][c:8]2[cH:9][c:... | CC(C)(C)OC(=O)N1CCC(Oc2cc(NC(=O)c3cccnc3Cl)cc(C(F)(F)F)c2)CC1.CN1CCC(COc2cc(N)ccc2C(C)(C)C)CC1 | CN1CCC(COc2cc(NC(=O)c3cccnc3Cl)ccc2C(C)(C)C)CC1 | null | null | null | Acylation | OtherReaction | 4a154f3d0451f7adc7e06eb20420593d6aae77ff8199bbf6d044af104e3f431a | 3a1146f373e13aeeb4978d04787fef10d7913789488cc4629f5b8b7a8a42f296 | O=C(Nc1cccc(OCC2CCNCC2)c1)c1cccnc1 | C-C(-C)(-C)-O-C(=O)-N1-C-C-C(-O-c2:c:c(-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8]):c:c(-C(-F)(-F)-F):c:2)-C-C-1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:4] | null | [] | null | null | null | null | N-[4-tert-Butyl-3-(1-methyl-piperidin-4-ylmethoxy)-phenyl]-2-chloro-nicotinamide was prepared from 4-tert-butyl-3-(1-methyl-piperidin-4-ylmethoxy)-phenylamine by a procedure similar to that described in the preparation of 1-Boc-4-{3-[(2-chloro-pyridine-3-carbonyl)-amino]-5-trifluoromethyl-phenoxy}-piperidine.
Condition... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carbamic ester.Ether.Ether.Secondary amide.Primary amine.Boc | Secondary amide | C1CCNCC1.c1ccccc1 | null | C1CC[NH]CC1.c1ccccc1.c1ccncc1 | HF | null | null | null | CC(C)(C)OC(=O)N1CCC(Oc2cc(NC(=O)c3cccnc3Cl)cc(C(F)(F)F)c2)CC1.CN1CCC(COc2cc(N)ccc2C(C)(C)C)CC1>>CN1CCC(COc2cc(NC(=O)c3cccnc3Cl)ccc2C(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb20fce2f941404db1e761c7c0fc4015 | CC(C)(C)c1ccc([N+](=O)[O-])cc1O.ClCCN1CCCCC1>>CC(C)(C)c1ccc([N+](=O)[O-])cc1OCCN1CCCCC1 | Cl.ClCCN1CCCCC1.C(=O)([O-])[O-].[K+].[K+].Cl.ClCCN1CCCCC1.C(C)(C)(C)C1=C(C=C(C=C1)[N+](=O)[O-])O.C(=O)([O-])[O-].[K+].[K+].CC(=O)C>>C(C)(C)(C)C1=C(OCCN2CCCCC2)C=C(C=C1)[N+](=O)[O-] | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[OH:14].Cl[CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[O:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][CH2:20][CH2:21][... | CC(C)(C)c1ccc([N+](=O)[O-])cc1O.ClCCN1CCCCC1 | CC(C)(C)c1ccc([N+](=O)[O-])cc1OCCN1CCCCC1 | null | CCCC[N+](CCCC)(CCCC)CCCC.[I-] | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCCN2CCCCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | To 2-tert-butyl-5-nitrophenol (1.01 g) and K2CO3 (1.72 g) was added acetone (35 ml) and H2O (10.5 mL), then 1-(2-chloroethyl)piperidine HCl (1.909 g) and TBAI (153 mg). The mixture was stirred at reflux overnight. Additional K2CO3 (850 mg) and 1-(2-chloroethyl)-piperidine HCl (950 mg) were added and the mixture was hea... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CC[NH]CC1 | HCl | CCCC[N+](CCCC)(CCCC)CCCC.[I-].O | null | null | CC(C)(C)c1ccc([N+](=O)[O-])cc1O.ClCCN1CCCCC1>CCCC[N+](CCCC)(CCCC)CCCC.[I-].O>CC(C)(C)c1ccc([N+](=O)[O-])cc1OCCN1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-853468a647964592914fef55bd0ff766 | CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CC1>>CC(C)(C)OC(=O)N1CCC(CO)CC1 | N1(CCOCC1)C(CO)C.C(C)OC(=O)C1CCN(CC1)C(=O)OC(C)(C)C>>C(=O)(OC(C)(C)C)N1CCC(CC1)CO | CCO[C:12]([CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:15][CH2:14]1)=[O:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][OH:13])[CH2:14][CH2:15]1 | CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CC1 | CC(C)(C)OC(=O)N1CCC(CO)CC1 | null | null | null | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CCNCC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[C:5]>>[C:4]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:5] | null | [] | null | null | null | null | 1-Boc-4-Hydroxymethyl-piperidine was prepared from 1-Boc-piperidine-4-carboxylic acid ethyl ester by a procedure similar to that described in the preparation of 2-morpholin-4-yl-propanol.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC[NH]CC1 | HO- | null | null | null | CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CC1>>CC(C)(C)OC(=O)N1CCC(CO)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd9bf937214e44e297797d92cd6baeda | CC(C)(C)OC(=O)N1CCC(CO)CC1.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)N1CCC(COS(C)(=O)=O)CC1 | C(=O)(OC(C)(C)C)N1CCC(CC1)CO.S(=O)(=O)(C)Cl>>C(=O)(OC(C)(C)C)N1CCC(CC1)COS(=O)(=O)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][OH:13])[CH2:18][CH2:19]1.Cl[S:14]([CH3:15])(=[O:16])=[O:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][O:13][S:14]([CH3:15])(=[O:16])=[O:17])[CH2:18][CH2:19]1 | CC(C)(C)OC(=O)N1CCC(CO)CC1.CS(=O)(=O)Cl | CC(C)(C)OC(=O)N1CCC(COS(C)(=O)=O)CC1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | C1CCNCC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | 0 | CELSIUS | 15 | MINUTE | Dissolved 1-Boc-4-hydroxymethyl-piperidine in anhydrous CH2Cl2 (50 ml) and TEA (4.5 ml) and cooled to 0° C. Mesyl chloride (840 μl) was added and the mixture was stirred for 15 min then at RT for 45 min. The mixture was washed with brine/1N HCl and then brine, dried over Na2SO4, concentrated in vacuo and dried under hi... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]CC1 | HCl | C(Cl)Cl | 0 | 0.25 | CC(C)(C)OC(=O)N1CCC(CO)CC1.CS(=O)(=O)Cl>C(Cl)Cl>CC(C)(C)OC(=O)N1CCC(COS(C)(=O)=O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5e253cb8a1ef4c40a26bddd3bc156d38 | CC(C)(C)OC(=O)N1CCC(COS(C)(=O)=O)CC1.O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(O)c1>>CC(C)(C)OC(=O)N1CCC(COc2cc([N+](=O)[O-])ccc2C(F)(F)C(F)(F)F)CC1 | C(=O)([O-])[O-].[K+].[K+].[H-].[Na+].[N+](=O)([O-])C=1C=CC(=C(C1)O)C(C(F)(F)F)(F)F.C(=O)(OC(C)(C)C)N1CCC(CC1)COS(=O)(=O)C>>C(=O)(OC(C)(C)C)N1CCC(CC1)COC1=CC(=CC=C1C(C(F)(F)F)(F)F)[N+](=O)[O-] | CS(=O)(=O)O[CH2:12][CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:31][CH2:30]1.[OH:13][c:14]1[cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21][c:22]1[C:23]([F:24])([F:25])[C:26]([F:27])([F:28])[F:29]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH... | CC(C)(C)OC(=O)N1CCC(COS(C)(=O)=O)CC1.O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(O)c1 | CC(C)(C)OC(=O)N1CCC(COc2cc([N+](=O)[O-])ccc2C(F)(F)C(F)(F)F)CC1 | null | null | CN(C)C=O.[OH-].[Na+] | Heteroatom Alkylation and Arylation | OtherReaction | 57201f1afbda3b7775282ca8e3c59a4fb8e542f888bbdbfa994f08238598f88e | b300ae9ac00448343b04f8595ac10c40ddc175401f75ad1a9cb423839305bb59 | c1ccc(OCC2CCNCC2)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:3]-[C:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8])-[C:4] | null | [] | null | null | 10 | MINUTE | To a slurry of 60% NaH suspension in DMF (30 mL) at RT added a solution of 5-nitro-2-pentafluoroethyl-phenol (3.6 g) in 5 mL DMF. The dark red mixture was stirred at RT for 10 min then added a solution of 1-Boc-4-methylsulfonyloxymethyl-piperidine (3.1 g) in 5 mL DMF. The reaction was stirred at 60° C. and 95° C. After... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic alcohol | Ether | null | null | C1CC[NH]CC1.c1ccccc1 | MsOH.HO- | CN(C)C=O.[OH-].[Na+] | null | 0.166667 | CC(C)(C)OC(=O)N1CCC(COS(C)(=O)=O)CC1.O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(O)c1>CN(C)C=O.[OH-].[Na+]>CC(C)(C)OC(=O)N1CCC(COc2cc([N+](=O)[O-])ccc2C(F)(F)C(F)(F)F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b2f37b5b369a4619a6d6a65e13db82a6 | CC(C)=O.O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(OCC2CCNCC2)c1>>CC(C)N1CCC(COc2cc([N+](=O)[O-])ccc2C(F)(F)C(F)(F)F)CC1 | CC(=O)O.[N+](=O)([O-])C=1C=CC(=C(OCC2CCNCC2)C1)C(C(F)(F)F)(F)F.CC(=O)C.CC(=O)C.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C)(C)N1CCC(CC1)COC1=C(C=CC(=C1)[N+](=O)[O-])C(C(F)(F)F)(F)F | O=[C:2]([CH3:1])[CH3:3].[NH:4]1[CH2:5][CH2:6][CH:7]([CH2:8][O:9][c:10]2[cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17][c:18]2[C:19]([F:20])([F:21])[C:22]([F:23])([F:24])[F:25])[CH2:26][CH2:27]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][O:9][c:10]2[cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]... | CC(C)=O.O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(OCC2CCNCC2)c1 | CC(C)N1CCC(COc2cc([N+](=O)[O-])ccc2C(F)(F)C(F)(F)F)CC1 | null | null | ClCCCl | Functional Group Addition | reductive amination | bdf3492dbea0a0e2fa2b9241cf6ccf0c5df69a797c0b4efc848998d30aeb7af2 | 2cf44c818c8ccfe8470f14fa07c7828891879f6644e8064bb35acc17d9c36b54 | c1ccc(OCC2CCNCC2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])-[C:7]-[C:8] | null | [] | null | null | 8 | HOUR | Dissolved 4-(5-nitro-2-pentafluoroethyl-phenoxymethyl)-piperidine (646 mg) in 1,2-dichloroethane (6.4 ml), then added acetone (136 ul), NaBH(OAc)3 (541 mg) and finally AcOH (105 ul). Stirred the cloudy yellow solution under N2 at RT overnight. Added another 130 uL acetone and stirred at RT over weekend. Quenched the re... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | Other | ClCCCl | null | 8 | CC(C)=O.O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(OCC2CCNCC2)c1>ClCCCl>CC(C)N1CCC(COc2cc([N+](=O)[O-])ccc2C(F)(F)C(F)(F)F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-51b3d1c1510e42a1b9e36193df81d854 | ClCCN1CCCC1.O=[N+]([O-])c1ccc(C(F)(F)F)c(O)c1>>O=[N+]([O-])c1ccc(C(F)(F)F)c(OCCN2CCCC2)c1 | [N+](=O)([O-])C=1C=CC(=C(C1)O)C(F)(F)F.ClCCN1CCCC1.C(C)(C)(C)C1=C(OCCN2CCCCC2)C=C(C=C1)[N+](=O)[O-]>>[N+](=O)([O-])C=1C=CC(=C(OCCN2CCCC2)C1)C(F)(F)F | Cl[CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[c:12]([OH:13])[cH:21]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[c:12]([O:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[cH:21]1 | ClCCN1CCCC1.O=[N+]([O-])c1ccc(C(F)(F)F)c(O)c1 | O=[N+]([O-])c1ccc(C(F)(F)F)c(OCCN2CCCC2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCCN2CCCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | 1-[2-(5-Nitro-2-trifluoromethylphenoxy)ethyl]-pyrrolidine was prepared from 5-nitro-2-trifluoromethyl-phenol and 1-(2-chloroethyl)pyrrolidine by a procedure similar to that described for 1-[2-(2-tert-butyl-5-nitro-phenoxy)-ethyl]-piperidine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CC[NH]C1 | HCl | null | null | null | ClCCN1CCCC1.O=[N+]([O-])c1ccc(C(F)(F)F)c(O)c1>>O=[N+]([O-])c1ccc(C(F)(F)F)c(OCCN2CCCC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ab3ee8f68a3e491d923b90186319c016 | ClCCN1CCCCC1.O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(O)c1>>O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(OCCN2CCCCC2)c1 | [N+](=O)([O-])C=1C=CC(=C(C1)O)C(C(F)(F)F)(F)F.ClCCN1CCCCC1.C(C)(C)(C)C1=C(OCCN2CCCCC2)C=C(C=C1)[N+](=O)[O-]>>[N+](=O)([O-])C=1C=CC(=C(OCCN2CCCCC2)C1)C(C(F)(F)F)(F)F | Cl[CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[F:14])[c:15]([OH:16])[cH:25]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[F:14])[c:15]([O:16][CH2:17][CH2:18][N:19]2[CH2:2... | ClCCN1CCCCC1.O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(O)c1 | O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(OCCN2CCCCC2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCCN2CCCCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | 1-[2-(5-Nitro-2-pentafluoroethyl-phenoxy)-ethyl]-piperidine was prepared from 5-nitro-2-pentafluoroethylphenol and 1-(2-chloroethyl)piperidine by a procedure similar to that described in the preparation of 1-[2-(2-tert-butyl-5-nitro-phenoxy)-ethyl]-piperidine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CC[NH]CC1 | HCl | null | null | null | ClCCN1CCCCC1.O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(O)c1>>O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(OCCN2CCCCC2)c1 |
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